Pesticidal pyrimidine compounds

ABSTRACT

Pyrimidine compounds and their use in controlling pests such as insects and other invertebrates are provided. Further embodiments, forms, objects, features, advantages, aspects and benefits shall become apparent from the description.

CROSS-REFERENCE TO RELATED APPLICATIONS

The present application is a continuation of U.S. patent applicationSer. No. 14/244,627 filed on Apr. 3, 2014, now U.S. Pat. No. 8,916,578,which claims priority to U.S. continuation application Ser. No.14/063,898 filed on Oct. 25, 2013, now U.S. Pat. No. 8,785,465, whichclaims priority to U.S. Provisional Patent Application No. 61/725,056filed on Nov. 12, 2012. The contents of these applications areincorporated herein by reference in their entirety.

FIELD OF THE INVENTION

The present application concerns novel pyrimidine compounds and theiruse in controlling pests such as insects and other invertebrates. Thepresent application also concerns novels procedures for preparing thesecompounds, pesticide compositions including these compounds, and methodsof controlling pests including insects using these compounds.

BACKGROUND OF THE INVENTION

Pests cause millions of human deaths around the world each year.Furthermore, there are more than ten thousand species of pests thatcause losses in agriculture. The world-wide agricultural losses amountto billions of U.S. dollars each year. Pests, such as termites, are alsoknown to cause damage to all kinds of private and public structuresresulting in billions of U.S. dollars in losses each year. Pests alsoeat and adulterate stored food. The world-wide stored food losses amountto billions of U.S. dollars each year, but more importantly, deprivepeople of needed food.

Certain pests have or are developing resistance to one or morepesticides in current use. Hundreds of pest species are resistant to oneor more pesticides. Accordingly, there exists a continuous need for newpesticides and for processes for forming such pesticides.

SUMMARY OF THE INVENTION

One embodiment disclosed herein concerns compounds useful for thecontrol of pests such as insects. Another embodiment concerns compoundsaccording to formula (I)

wherein:

R¹ is selected from the group consisting of hydrogen and halogen;

R² is selected from the group consisting of hydrogen, substituted orunsubstituted C₁-C₆ alkyl, substituted or unsubstituted C₂-C₆ alkenyl,substituted or unsubstituted C₁-C₆ haloalkyl, substituted orunsubstituted C₁-C₆ acyl, substituted or unsubstituted C₁-C₆carboalkoxy, carboxylic acid, substituted or unsubstituted C₂-C₆alkenyloxy, substituted or unsubstituted C₁-C₆ alkoxy, substituted orunsubstituted C₃-C₆ alkynyl, substituted or unsubstituted C₃-C₆alkynyloxy, substituted or unsubstituted C₃-C₁₀ aryl, substituted orunsubstituted C₁-C₁₀ aryloxy, substituted or unsubstituted C₃-C₁₀cycloalkenyl, substituted or unsubstituted C₃-C₁₀ cycloalkenyloxy,substituted or unsubstituted C₃-C₁₀ cycloalkyl, substituted orunsubstituted C₃-C₁₀ cycloalkoxy, halo, and substituted or unsubstitutedC₁-C₁₀ heterocyclyl;

R³ is selected from the group consisting of hydrogen, substituted orunsubstituted C₁-C₆ alkyl, substituted or unsubstituted C₂-C₆ alkenyl,substituted or unsubstituted C₁-C₆ haloalkyl, substituted orunsubstituted C₃-C₆ acyl, substituted or unsubstituted C₁-C₆carboalkoxy, carboxylic acid, substituted or unsubstituted C₂-C₆alkenyloxy, substituted or unsubstituted C₁-C₆ alkoxy, substituted orunsubstituted C₃-C₆ alkynyl, substituted or unsubstituted C₃-C₆alkynyloxy, substituted or unsubstituted C₃-C₁₀ aryl, substituted orunsubstituted C₃-C₁₀ aryloxy, substituted or unsubstituted C₃-C₁₀cycloalkenyl, substituted or unsubstituted C₃-C₁₀ cycloalkenyloxy,substituted or unsubstituted C₃-C₁₀ cycloalkyl, substituted orunsubstituted C₃-C₁₀ cycloalkoxy, halo, and substituted or unsubstitutedC₁-C₁₀ heterocyclyl;

each of R⁴, R⁵, and R⁶ is independently selected from the groupconsisting of hydrogen, halogen, substituted or unsubstituted C₁-C₆alkyl, substituted or unsubstituted C₂-C₆ alkenyl, substituted orunsubstituted C₁-C₆ haloalkyl, substituted or unsubstituted C₁-C₆ acyl,substituted or unsubstituted C₁-C₆ carboalkoxy, carboxylic acid,substituted or unsubstituted C₂-C₆ alkenyloxy, substituted orunsubstituted C₁-C₆ alkoxy, substituted or unsubstituted C₃-C₆ alkynyl,substituted or unsubstituted C₃-C₆ alkynyloxy, substituted orunsubstituted C₃-C₁₀ aryl, substituted or unsubstituted C₁-C₁₀ aryloxy,substituted or unsubstituted C₃-C₁₀ cycloalkenyl, substituted orunsubstituted C₃-C₁₀ cycloalkenyloxy, substituted or unsubstitutedC₃-C₁₀ cycloalkyl, substituted or unsubstituted C₃-C₁₀ cycloalkoxy,substituted or unsubstituted C₁-C₆ nitriles, substituted orunsubstituted C₁-C₆ amides, substituted or unsubstituted C₁-C₆ amines, S(substituted or unsubstituted C₁-C₆ alkyl), S(O)_(n) (substituted orunsubstituted C₁-C₆ alkyl) wherein n=0, 1 or 2, and substituted orunsubstituted C₁-C₁₀ heterocyclyl; and

each R⁷ is independently selected from the group consisting of halogen,substituted or unsubstituted C₁-C₆ alkyl, substituted or unsubstitutedC₂-C₆ alkenyl, substituted or unsubstituted C₁-C₆ haloalkyl, substitutedor unsubstituted C₁-C₆ acyl, substituted or unsubstituted C₁-C₆carboalkoxy, carboxylic acid, substituted or unsubstituted substitutedor unsubstituted C₂-C₆ alkenyloxy, substituted or unsubstituted C₁-C₆alkoxy, substituted or unsubstituted C₃-C₆ alkynyl, substituted orunsubstituted C₃-C₆ alkynyloxy, substituted or unsubstituted C₃-C₁₀aryl, substituted or unsubstituted C₁-C₁₀ aryloxy, substituted orunsubstituted C₃-C₁₀ cycloalkenyl, substituted or unsubstituted C₃-C₁₀cycloalkenyloxy, substituted or unsubstituted C₃-C₁₀ cycloalkyl,substituted or unsubstituted C₃-C₁₀ cycloalkoxy, and substituted orunsubstituted C₁-C₁₀ heterocyclyl, wherein each substituted orunsubstituted substituent may be independently substituted with one ormore of the following substituents F, Cl, Br, I, CN, NO₂, C₁-C₆ alkyl,C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ alkoxy, C₁-C₆ haloalkyl, C₁-C₆haloalkoxy, C₁-C₆ haloalkylthio, S(═O)_(n1)C₁-C₆ alkyl (where n1=0-2),S(═O)_(n1)C₁-C₆ haloalkyl (where n1=0-2), OSO₂C₁-C₆ haloalkyl,C(═O)OC₁-C₆ alkyl, C(═O)C₁-C₆ alkyl, C(═O)C₁-C₆ haloalkyl, aryl, C₁-C₆hydroxyalkyl, CO₂R⁸, wherein R⁸ is a C₁-C₆ alkyl, and heterocyclyl.

More particular but non-limiting forms of compounds according to formula(I) include the following classes:

(1) Compounds of formula (I) wherein R¹ represents H or halogen.

(2) Compounds of formula (I) wherein R² represents H or a substituted orunsubstituted C₁-C₆ alkoxy.

(3) Compounds of formula (I) wherein R³ represents H, a substituted orunsubstituted C₁-C₆ alkyl, or a substituted or unsubstituted C₁-C₆alkoxy.

(4) Compounds of formula (I) wherein R⁴ represents H, halogen, asubstituted or unsubstituted C₁-C₆ alkyl, a substituted or unsubstitutedC₁-C₆ nitrile, or a substituted or unsubstituted C₃-C₁₀ cycloalkenyl, orwherein R⁴ represents H, halogen, a substituted or unsubstituted C₁-C₆alkyl, or a substituted or unsubstituted C₃-C₁₀ cycloalkenyl.

(5) Compounds of formula (I) wherein R⁵ represents H, halogen, asubstituted or unsubstituted C₁-C₆ haloalkyl, a substituted orunsubstituted C₁-C₆ alkyl, or a substituted or unsubstituted C₁-C₆nitrile.

(6) Compounds of formula (I) wherein R⁶ represents H, halogen, asubstituted or unsubstituted C₁-C₆ alkyl, or a substituted orunsubstituted C₁-C₆ alkoxy.

(7) Compounds of formula (I) wherein R⁷ represents halogen.

It should be understood by those skilled in the art that one or morecombinations of the above described classes 1-7 of the compoundaccording to formula (I) are possible. Stated alternatively, in somemore particular but non-limiting forms of compounds according to formula(I), one or more or all of R¹-R⁷ may represent a substituent listed in arespective one of classes 1-7.

Additional, more particular but non-limiting forms of compoundsaccording to formula (I) include the following classes:

(8) Compounds of formula (I) wherein R¹ represents H or halogen.

(9) Compounds of formula (I) wherein R² represents H or a substituted orunsubstituted C₁-C₆ alkoxy.

(10) Compounds of formula (I) wherein R³ represents H, a substituted orunsubstituted C₁-C₆ alkyl, or a substituted or unsubstituted C₁-C₆alkoxy.

(11) Compounds of formula (I) wherein R⁴ represents H.

(12) Compounds of formula (I) wherein R⁵ represents a substituted orunsubstituted C₁-C₆ haloalkyl such as CF₃.

(13) Compounds of formula (I) wherein R⁶ represents H.

(14) Compounds of formula (I) wherein R⁷ represents halogen.

It should be understood by those skilled in the art that one or morecombinations of the above described classes 9-14 of the compoundaccording to formula (I) are possible. Stated alternatively, in somemore particular but non-limiting forms of compounds according to formula(I), one or more or all of R¹-R⁷ may represent a substituent listed in arespective one of classes 9-14.

Another embodiment concerns compounds according to formula (I) havingthe following structure:

wherein:

R¹ represents H or halogen;

R² represents H, CH₂OCH₃, CH₂OC(═O)CH₃ or CH₂OCH₂R⁹, wherein R⁹represents

R³ represents H, methyl, CH₂OCH₃, or CH₂OCH₂R⁹, wherein R⁹ represents

R⁴ represents H, halogen, methyl, CN, or

R⁵ represents H, halogen, CN, methyl, ethyl or C(R¹⁰)₃, wherein R¹⁰represents halogen; and

R⁶ represents H, halogen, methyl or OCH₃.

More particular but non-limiting forms of this embodiment include thefollowing classes:

(15) Compounds where R⁵ represents CF₃.

(16) Compounds where R¹ represents H or F.

(17) Compounds where R⁴ and R⁶ represent H.

(18) Compounds where R² and R³ represent H.

It should be understood by those skilled in the art that one or morecombinations of the above described classes 15-18 are possible.

In further, more particular but non-limiting forms of this embodiment,R¹-R⁶ represent the following:

R¹ represents H or F;

R² represents H, CH₂OCH₃, CH₂OC(═O)CH₃ or CH₂OCH₂R⁹, wherein R⁹represents

R³ represents H, methyl or CH₂OCH₃;

R⁴ represents H, methyl, Cl or

R⁵ represents H, Cl, CN, methyl or CF₃; and

R⁶ represents H, methyl, Cl or OCH₃.

In even further, more particular but non-limiting forms of thisembodiment, R¹-R⁶ represent the following:

R¹ represents H or F;

R² represents H, CH₂OCH₃, CH₂OC(═O)CH₃ or CH₂OCH₂R⁹, wherein R⁹represents

R³ represents H, methyl or CH₂OCH₃;

R⁴ represents H;

R⁵ represents CF₃; and

R⁶ represents H.

Further aspects, embodiments, forms, features, benefits, objects andadvantages shall become apparent from the detailed description providedherewith.

DETAILED DESCRIPTION OF THE INVENTION

For purposes of promoting an understanding of the invention, referencewill now be made to the following embodiments and specific language willbe used to describe the same. It will nevertheless be understood that nolimitation of the scope of the invention is thereby intended, suchalterations and further modifications in the described subject matter,and such further applications of the principles of the invention asdescribed herein being contemplated as would normally occur to oneskilled in the art to which the invention relates.

DEFINITIONS

The examples given in the definitions are generally non-exhaustive andmust not be construed as limiting the invention disclosed in thisdocument. It is understood that a substituent should comply withchemical bonding rules and steric compatibility constraints in relationto the particular molecule to which it is attached.

“Alkenyl” means an acyclic, unsaturated (at least one carbon-carbondouble bond), branched or unbranched, substituent consisting of carbonand hydrogen, for example, vinyl, allyl, butenyl, pentenyl, and hexenyl.

“Alkenyloxy” means an alkenyl further consisting of a carbon-oxygensingle bond, for example, allyloxy, butenyloxy, pentenyloxy, hexenyloxy.

“Alkoxy” means an alkyl further consisting of a carbon-oxygen singlebond, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy,isobutoxy, and tert-butoxy.

“Alkyl” means an acyclic, saturated, branched or unbranched, substituentconsisting of carbon and hydrogen, for example, methyl, ethyl, propyl,isopropyl, butyl, and tert-butyl.

“Alkynyl” means an acyclic, unsaturated (at least one carbon-carbontriple bond), branched or unbranched, substituent consisting of carbonand hydrogen, for example, ethynyl, propargyl, butyryl, and pentynyl.

“Alkynyloxy” means an alkynyl further consisting of a carbon-oxygensingle bond, for example, pentynyloxy, hexynyloxy, heptynyloxy, andoctynyloxy.

“Aryl” means a cyclic, aromatic substituent consisting of hydrogen andcarbon, for example, phenyl, naphthyl, and biphenyl.

“Cycloalkenyl” means a monocyclic or polycyclic, unsaturated (at leastone carbon-carbon double bond) substituent consisting of carbon andhydrogen, for example, cyclobutenyl, cyclopentenyl, cyclohexenyl,norbornenyl, bicyclo[2.2.2]octenyl, tetrahydronaphthyl,hexahydronaphthyl, and octahydronaphthyl.

“Cycloalkenyloxy” means a cycloalkenyl further consisting of acarbon-oxygen single bond, for example, cyclobutenyloxy,cyclopentenyloxy, norbornenyloxy, and bicyclo[2.2.2]octenyloxy.

“Cycloalkyl” means a monocyclic or polycyclic, saturated substituentconsisting of carbon and hydrogen, for example, cyclopropyl, cyclobutyl,cyclopentyl, norbornyl, bicyclo[2.2.2]octyl, and decahydronaphthyl.

“Cycloalkoxy” means a cycloalkyl further consisting of a carbon-oxygensingle bond, for example, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy,norbornyloxy, and bicyclo[2.2.2]octyloxy.

“Halo” or “Halogen” means fluoro, chloro, bromo, and iodo. “Haloalkoxy”means an alkoxy further consisting of, from one to the maximum possiblenumber of identical or different, halos, for example, fluoromethoxy,trifluoromethoxy, 2,2-difluoropropoxy, chloromethoxy, trichloromethoxy,1,1,2,2-tetrafluoroethoxy, and pentafluoroethoxy.

“Haloalkyl” means an alkyl further consisting of, from one to themaximum possible number of, identical or different, halos, for example,fluoromethyl, trifluoromethyl, 2,2-difluoropropyl, chloromethyl,trichloromethyl, and 1,1,2,2-tetrafluoroethyl.

“Heterocyclyl” means a cyclic substituent that may be fully saturated,partially unsaturated, or fully unsaturated, where the cyclic structurecontains at least one carbon and at least one heteroatom, where saidheteroatom is nitrogen, sulfur, or oxygen. Examples of aromaticheterocyclyls include, but are not limited to, benzofuranyl,benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, benzothienyl,benzothiazolyl cinnolinyl, furanyl, indazolyl, indolyl, imidazolyl,isoindolyl, isoquinolinyl, isothiazolyl, isoxazolyl, oxadiazolyl,oxazolinyl, oxazolyl, phthalazinyl, pyrazinyl, pyrazolinyl, pyrazolyl,pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, quinazolinyl, quinolinyl,quinoxalinyl, tetrazolyl, thiazolinyl, thiazolyl, thienyl, triazinyl,and triazolyl. Examples of fully saturated heterocyclyls include, butare not limited to, piperazinyl, piperidinyl, morpholinyl, pyrrolidinyl,tetrahydrofuranyl, and tetrahydropyranyl. Examples of partiallyunsaturated heterocyclyls include, but are not limited to,1,2,3,4-tetrahydro-quinolinyl, 4,5-dihydro-oxazolyl,4,5-dihydro-1H-pyrazolyl, 4,5-dihydro-isoxazolyl, and2,3-dihydro-[1,3,4]-oxadiazolyl.

One embodiment disclosed herein is related to novel pyrimidine compoundsand their use in controlling pests such as insects and otherinvertebrates. Another more particular but non-exclusive embodiment isrelated to compounds according to formula (I):

wherein

R¹ is selected from the group consisting of hydrogen and halogen;

R² is selected from the group consisting of hydrogen, substituted orunsubstituted C₁-C₆ alkyl, substituted or unsubstituted C₂-C₆ alkenyl,substituted or unsubstituted C₁-C₆ haloalkyl, substituted orunsubstituted C₁-C₆ acyl, substituted or unsubstituted C₁-C₆carboalkoxy, carboxylic acid, substituted or unsubstituted C₂-C₆alkenyloxy, substituted or unsubstituted C₁-C₆ alkoxy, substituted orunsubstituted C₃-C₆ alkynyl, substituted or unsubstituted C₃-C₆alkynyloxy, substituted or unsubstituted C₃-C₁₀ aryl, substituted orunsubstituted C₁-C₁₀ aryloxy, substituted or unsubstituted C₃-C₁₀cycloalkenyl, substituted or unsubstituted C₃-C₁₀ cycloalkenyloxy,substituted or unsubstituted C₃-C₁₀ cycloalkyl, substituted orunsubstituted C₃-C₁₀ cycloalkoxy, halo, and substituted or unsubstitutedC₁-C₁₀ heterocyclyl;

R³ is selected from the group consisting of hydrogen, substituted orunsubstituted C₁-C₆ alkyl, substituted or unsubstituted C₂-C₆ alkenyl,substituted or unsubstituted C₁-C₆ haloalkyl, substituted orunsubstituted C₃-C₆ acyl, substituted or unsubstituted C₁-C₆carboalkoxy, carboxylic acid, substituted or unsubstituted C₂-C₆alkenyloxy, substituted or unsubstituted C₁-C₆ alkoxy, substituted orunsubstituted C₃-C₆ alkynyl, substituted or unsubstituted C₃-C₆alkynyloxy, substituted or unsubstituted C₃-C₁₀ aryl, substituted orunsubstituted C₃-C₁₀ aryloxy, substituted or unsubstituted C₃-C₁₀cycloalkenyl, substituted or unsubstituted C₃-C₁₀ cycloalkenyloxy,substituted or unsubstituted C₃-C₁₀ cycloalkyl, substituted orunsubstituted C₃-C₁₀ cycloalkoxy, halo, and substituted or unsubstitutedC₁-C₁₀ heterocyclyl;

each of R⁴, R⁵, and R⁶ is independently selected from the groupconsisting of hydrogen, halogen, substituted or unsubstituted C₁-C₆alkyl, substituted or unsubstituted C₂-C₆ alkenyl, substituted orunsubstituted C₁-C₆ haloalkyl, substituted or unsubstituted C₁-C₆ acyl,substituted or unsubstituted C₁-C₆ carboalkoxy, carboxylic acid,substituted or unsubstituted C₂-C₆ alkenyloxy, substituted orunsubstituted C₁-C₆ alkoxy, substituted or unsubstituted C₃-C₆ alkynyl,substituted or unsubstituted C₃-C₆ alkynyloxy, substituted orunsubstituted C₃-C₁₀ aryl, substituted or unsubstituted C₁-C₁₀ aryloxy,substituted or unsubstituted C₃-C₁₀ cycloalkenyl, substituted orunsubstituted C₃-C₁₀ cycloalkenyloxy, substituted or unsubstitutedC₃-C₁₀ cycloalkyl, substituted or unsubstituted C₃-C₁₀ cycloalkoxy,substituted or unsubstituted C₁-C₆ nitriles, substituted orunsubstituted C₁-C₆ amides, substituted or unsubstituted C₁-C₆ amines, S(substituted or unsubstituted C₁-C₆ alkyl), S(O)_(n) (substituted orunsubstituted C₁-C₆ alkyl) wherein n=0, 1 or 2, and substituted orunsubstituted C₁-C₁₀ heterocyclyl; and

each R⁷ is independently selected from the group consisting of halogen,substituted or unsubstituted C₁-C₆ alkyl, substituted or unsubstitutedC₂-C₆ alkenyl, substituted or unsubstituted C₁-C₆ haloalkyl, substitutedor unsubstituted C₁-C₆ acyl, substituted or unsubstituted C₁-C₆carboalkoxy, carboxylic acid, substituted or unsubstituted substitutedor unsubstituted C₂-C₆ alkenyloxy, substituted or unsubstituted C₁-C₆alkoxy, substituted or unsubstituted C₃-C₆ alkynyl, substituted orunsubstituted C₃-C₆ alkynyloxy, substituted or unsubstituted C₃-C₁₀aryl, substituted or unsubstituted C₁-C₁₀ aryloxy, substituted orunsubstituted C₃-C₁₀ cycloalkenyl, substituted or unsubstituted C₃-C₁₀cycloalkenyloxy, substituted or unsubstituted C₃-C₁₀ cycloalkyl,substituted or unsubstituted C₃-C₁₀ cycloalkoxy, and substituted orunsubstituted C₁-C₁₀ heterocyclyl, wherein each substituted orunsubstituted substituent may be independently substituted with one ormore of the following substituents F, Cl, Br, I, CN, NO₂, C₁-C₆ alkyl,C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ alkoxy, C₁-C₆ haloalkyl, C₁-C₆haloalkoxy, C₁-C₆ haloalkylthio, S(═O)_(n1)C₁-C₆ alkyl (where n1=0-2),S(═O)_(n1)C₁-C₆ haloalkyl (where n1=0-2), OSO₂C₁-C₆ haloalkyl,C(═O)OC₁-C₆ alkyl, C(═O)C₁-C₆ alkyl, C(═O)C₁-C₆ haloalkyl, aryl, C₁-C₆hydroxyalkyl, CO₂R⁸, wherein R⁸ is C₁-C₆ alkyl, and heterocyclyl. Moreparticular but non-limiting forms of compounds according to formula (I)include the following classes:

(1) Compounds of formula (I) wherein R¹ represents H or halogen.

(2) Compounds of formula (I) wherein R² represents H or a substituted orunsubstituted C₁-C₆ alkoxy.

(3) Compounds of formula (I) wherein R³ represents H, a substituted orunsubstituted C₁-C₆ alkyl, or a substituted or unsubstituted C₁-C₆alkoxy.

(4) Compounds of formula (I) wherein R⁴ represents H, halogen, asubstituted or unsubstituted C₁-C₆ alkyl, a substituted or unsubstitutedC₁-C₆ nitrile, or a substituted or unsubstituted C₃-C₁₀ cycloalkenyl, orwherein R⁴ represents H, halogen, a substituted or unsubstituted C₁-C₆alkyl, or a substituted or unsubstituted C₃-C₁₀ cycloalkenyl.

(5) Compounds of formula (I) wherein R⁵ represents H, halogen, asubstituted or unsubstituted C₁-C₆ haloalkyl, a substituted orunsubstituted C₁-C₆ alkyl, or a substituted or unsubstituted C₁-C₆nitrile.

(6) Compounds of formula (I) wherein R⁶ represents H, halogen, asubstituted or unsubstituted C₁-C₆ alkyl, or a substituted orunsubstituted C₁-C₆ alkoxy.

(7) Compounds of formula (I) wherein R⁷ represents halogen.

It should be understood by those skilled in the art that one or morecombinations of the above described classes 1-7 of the compoundaccording to formula (I) are possible. Stated alternatively, in somemore particular but non-limiting forms of compounds according to formula(I), one or more or all of R¹-R⁷ may represent a substituent listed in arespective one of classes 1-7.

Additional, more particular but non-limiting forms of compoundsaccording to formula (I) include the following classes:

(8) Compounds of formula (I) wherein R¹ represents H or halogen.

(9) Compounds of formula (I) wherein R² represents H or a substituted orunsubstituted C₁-C₆ alkoxy.

(10) Compounds of formula (I) wherein R³ represents H, a substituted orunsubstituted C₁-C₆ alkyl, or a substituted or unsubstituted C₁-C₆alkoxy.

(11) Compounds of formula (I) wherein R⁴ represents H.

(12) Compounds of formula (I) wherein R⁵ represents a substituted orunsubstituted C₁-C₆ haloalkyl such as CF₃.

(13) Compounds of formula (I) wherein R⁶ represents H.

(14) Compounds of formula (I) wherein R⁷ represents halogen.

It should be understood by those skilled in the art that one or morecombinations of the above described classes 9-14 of the compoundaccording to formula (I) are possible. Stated alternatively, in somemore particular but non-limiting forms of compounds according to formula(I), one or more or all of R¹-R⁷ may represent a substituent listed in arespective one of classes 9-14.

Another embodiment concerns compounds according to formula (I) havingthe following structure:

wherein:

R¹ represents H or halogen;

R² represents H, CH₂OCH₃, CH₂OC(═O)CH₃ or CH₂OCH₂R⁹, wherein R⁹represents

R³ represents H, methyl, CH₂OCH₃, or CH₂OCH₂R⁹, wherein R⁹ represents

R⁴ represents H, halogen, methyl, CN, or

R⁵ represents H, halogen, CN, methyl, ethyl or C(R¹⁰)₃, wherein R¹⁰represents halogen; and

R⁶ represents H, halogen, methyl or OCH₃.

More particular but non-limiting forms of this embodiment include thefollowing classes:

(15) Compounds where R⁵ represents CF₃.

(16) Compounds where R¹ represents H or F.

(17) Compounds where R⁴ and R⁶ represent H.

(18) Compounds where R² and R³ represent H.

It should be understood by those skilled in the art that one or morecombinations of the above described classes 15-18 are possible.

In further, more particular but non-limiting forms of this embodiment,R¹-R⁶ represent the following:

R¹ represents H or F;

R² represents H, CH₂OCH₃, CH₂OC(═O)CH₃ or CH₂OCH₂R⁹, wherein R⁹represents

R³ represents H, methyl or CH₂OCH₃;

R⁴ represents H, methyl, Cl or

R⁵ represents H, Cl, CN, methyl or CF₃; and

R⁶ represents H, methyl, Cl or OCH₃.

In even further, more particular but non-limiting forms of thisembodiment, R¹-R⁶ represent the following:

R¹ represents H or F;

R² represents H, CH₂OCH₃, CH₂OC(═O)CH₃ or CH₂OCH₂R⁹, wherein R⁹represents

R³ represents H, methyl or CH₂OCH₃;

R⁴ represents H;

R⁵ represents CF₃; and

R⁶ represents H.

Pesticidally Acceptable Acid Addition Salts, Salt Derivatives, Solvates,Ester Derivatives, Polymorphs, Isotopes and Radionuclides

Compounds according to formula (I) may be formulated into pesticidallyacceptable acid addition salts. By way of a non-limiting example, anamine function can form salts with hydrochloric, hydrobromic, sulfuric,phosphoric, acetic, benzoic, citric, malonic, salicylic, malic, fumaric,oxalic, succinic, tartaric, lactic, gluconic, ascorbic, maleic,aspartic, benzenesulfonic, methanesulfonic, ethanesulfonic,hydroxymethanesulfonic, and hydroxyethanesulfonic acids. Additionally,by way of a non-limiting example, an acid function can form saltsincluding those derived from alkali or alkaline earth metals and thosederived from ammonia and amines. Exemplary cations include sodium,potassium, and magnesium.

Compounds according to formula (I) may be formulated into saltderivatives. By way of a non-limiting example, a salt derivative can beprepared by contacting a free base with a sufficient amount of thedesired acid to produce a salt. A free base may be regenerated bytreating the salt with a suitable dilute aqueous base solution such asdilute aqueous sodium hydroxide (NaOH), potassium carbonate, ammonia,and sodium bicarbonate. As an example, in many cases, a pesticide, suchas 2,4-D, is made more water-soluble by converting it to itsdimethylamine salt.

Compounds according to formula (I) may be formulated into stablecomplexes with a solvent, such that the complex remains intact after thenon-complexed solvent is removed. These complexes are often referred toas “solvates.” However, in one particular form, stable hydrates areformed with water as the solvent.

Compounds according to formula (I) may be made into ester derivatives.These ester derivatives can then be applied in the same manner as themolecules disclosed in this document is applied.

Compounds according to formula (I) may be made as various crystalpolymorphs. Polymorphism is important in the development ofagrochemicals since different crystal polymorphs or structures of thesame molecule can have vastly different physical properties andbiological performances.

Compounds according to formula (I) may be made with different isotopes.Particular but non-limiting examples of such are molecules having ²H(also known as deuterium) in place of ¹H.

Compounds according to formula (I) may be made with differentradionuclides. Particular but non-limiting examples of such aremolecules having ¹⁴C.

Combinations

Compounds according to formula (I) may also be used in combination (suchas, in a compositional mixture, or a simultaneous or sequentialapplication) with one or more compounds having acaricidal, algicidal,avicidal, bactericidal, fungicidal, herbicidal, insecticidal,molluscicidal, nematicidal, rodenticidal, or virucidal properties.Additionally, compounds according to formula (I) may also be used incombination (such as, in a compositional mixture, or a simultaneous orsequential application) with compounds that are antifeedants, birdrepellents, chemosterilants, herbicide safeners, insect attractants,insect repellents, mammal repellents, mating disrupters, plantactivators, plant growth regulators, or synergists. Examples of suchcompounds in the above groups that may be used with compounds accordingto formula (I) are—(3-ethoxypropyl)mercury bromide, 1,2-dichloropropane,1,3-dichloropropene, 1-methylcyclopropene, 1-naphthol,2-(octylthio)ethanol, 2,3,5-tri-iodobenzoic acid, 2,3,6-TBA,2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA-potassium,2,3,6-TBA-sodium, 2,4,5-T, 2,4,5-T-2-butoxypropyl, 2,4,5-T-2-ethylhexyl,2,4,5-T-3-butoxypropyl, 2,4,5-TB, 2,4,5-T-butometyl, 2,4,5-T-butotyl,2,4,5-T-butyl, 2,4,5-T-isobutyl, 2,4,5-T-isoctyl, 2,4,5-T-isopropyl,2,4,5-T-methyl, 2,4,5-T-pentyl, 2,4,5-T-sodium,2,4,5-T-triethylammonium, 2,4,5-T-trolamine, 2,4-D,2,4-D-2-butoxypropyl, 2,4-D-2-ethylhexyl, 2,4-D-3-butoxypropyl,2,4-D-ammonium, 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium,2,4-DB-isoctyl, 2,4-DB-potassium, 2,4-DB-sodium, 2,4-D-butotyl,2,4-D-butyl, 2,4-D-diethylammonium, 2,4-D-dimethylammonium,2,4-D-diolamine, 2,4-D-dodecylammonium, 2,4-DEB, 2,4-DEP, 2,4-D-ethyl,2,4-D-heptylammonium, 2,4-D-isobutyl, 2,4-D-isoctyl, 2,4-D-isopropyl,2,4-D-isopropylammonium, 2,4-D-lithium, 2,4-D-meptyl, 2,4-D-methyl,2,4-D-octyl, 2,4-D-pentyl, 2,4-D-potassium, 2,4-D-propyl, 2,4-D-sodium,2,4-D-tefuryl, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium,2,4-D-tris(2-hydroxypropyl)ammonium, 2,4-D-trolamine, 2iP,2-methoxyethylmercury chloride, 2-phenylphenol, 3,4-DA, 3,4-DB, 3,4-DP,4-aminopyridine, 4-CPA, 4-CPA-potassium, 4-CPA-sodium, 4-CPB, 4-CPP,4-hydroxyphenethyl alcohol, 8-hydroxyquinoline sulfate,8-phenylmercurioxyquinoline, abamectin, abscisic acid, ACC, acephate,acequinocyl, acetamiprid, acethion, acetochlor, acetophos, acetoprole,acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-methyl,acifluorfen-sodium, aclonifen, acrep, acrinathrin, acrolein,acrylonitrile, acypetacs, acypetacs-copper, acypetacs-zinc, alachlor,alanycarb, albendazole, aldicarb, aldimorph, aldoxycarb, aldrin,allethrin, allicin, allidochlor, allosamidin, alloxydim,alloxydim-sodium, allyl alcohol, allyxycarb, alorac, alpha-cypermethrin,alpha-endosulfan, ametoctradin, ametridione, ametryn, amibuzin,amicarbazone, amicarthiazol, amidithion, amidoflumet, amidosulfuron,aminocarb, aminocyclopyrachlor, aminocyclopyrachlor-methyl, aminocyclopyrachlor-potassium, aminopyralid, aminopyralid-potassium,aminopyralid-tris(2-hydroxypropyl)ammonium, amiprofos-methyl,amiprophos, amisulbrom, amiton, amiton oxalate, amitraz, amitrole,ammonium sulfamate, ammonium α-naphthaleneacetate, amobam, ampropylfos,anabasine, ancymidol, anilazine, anilofos, anisuron, anthraquinone,antu, apholate, aramite, arsenous oxide, asomate, aspirin, asulam,asulam-potassium, asulam-sodium, athidathion, atraton, atrazine,aureofungin, aviglycine, aviglycine hydrochloride, azaconazole,azadirachtin, azafenidin, azamethiphos, azimsulfuron, azinphos-ethyl,azinphos-methyl, aziprotryne, azithiram, azobenzene, azocyclotin,azothoate, azoxystrobin, bachmedesh, barban, barium hexafluorosilicate,barium polysulfide, barthrin, BCPC, beflubutamid, benalaxyl,benalaxyl-M, benazolin, benazolin-dimethylammonium, benazolin-ethyl,benazolin-potassium, bencarbazone, benclothiaz, bendiocarb, benfluralin,benfuracarb, benfuresate, benodanil, benomyl, benoxacor, benoxafos,benquinox, bensulfuron, bensulfuron-methyl, bensulide, bensultap,bentaluron, bentazone, bentazone-sodium, benthiavalicarb,benthiavalicarb-isopropyl, benthiazole, bentranil, benzadox,benzadox-ammonium, benzalkonium chloride, benzamacril,benzamacril-isobutyl, benzamorf, benzfendizone, benzipram,benzobicyclon, benzofenap, benzofluor, benzohydroxamic acid,benzoximate, benzoylprop, benzoylprop-ethyl, benzthiazuron, benzylbenzoate, benzyladenine, berberine, berberine chloride, beta-cyfluthrin,beta-cypermethrin, bethoxazin, bicyclopyrone, bifenazate, bifenox,bifenthrin, bifujunzhi, bilanafos, bilanafos-sodium, binapacryl,bingqingxiao, bioallethrin, bioethanomethrin, biopermethrin,bioresmethrin, biphenyl, bisazir, bismerthiazol, bispyribac,bispyribac-sodium, bistrifluron, bitertanol, bithionol, bixafen,blasticidin-S, borax, Bordeaux mixture, boric acid, boscalid,brassinolide, brassinolide-ethyl, brevicomin, brodifacoum,brofenvalerate, brofluthrinate, bromacil, bromacil-lithium,bromacil-sodium, bromadiolone, bromethalin, bromethrin, bromfenvinfos,bromoacetamide, bromobonil, bromobutide, bromocyclen, bromo-DDT,bromofenoxim, bromophos, bromophos-ethyl, bromopropylate, bromothalonil,bromoxynil, bromoxynil butyrate, bromoxynil heptanoate, bromoxyniloctanoate, bromoxynil-potassium, brompyrazon, bromuconazole, bronopol,bucarpolate, bufencarb, buminafos, bupirimate, buprofezin, Burgundymixture, busulfan, butacarb, butachlor, butafenacil, butamifos,butathiofos, butenachlor, butethrin, buthidazole, buthiobate, buthiuron,butocarboxim, butonate, butopyronoxyl, butoxycarboxim, butralin,butroxydim, buturon, butylamine, butylate, cacodylic acid, cadusafos,cafenstrole, calcium arsenate, calcium chlorate, calcium cyanamide,calcium polysulfide, calvinphos, cambendichlor, camphechlor, camphor,captafol, captan, carbamorph, carbanolate, carbaryl, carbasulam,carbendazim, carbendazim benzenesulfonate, carbendazim sulfite,carbetamide, carbofuran, carbon disulfide, carbon tetrachloride,carbophenothion, carbosulfan, carboxazole, carboxide, carboxin,carfentrazone, carfentrazone-ethyl, carpropamid, cartap, cartaphydrochloride, carvacrol, carvone, CDEA, cellocidin, CEPC, ceralure,Cheshunt mixture, chinomethionat, chitosan, chlobenthiazone,chlomethoxyfen, chloralose, chloramben, chloramben-ammonium,chloramben-diolamine, chloramben-methyl, chloramben-methylammonium,chloramben-sodium, chloramine phosphorus, chloramphenicol,chloraniformethan, chloranil, chloranocryl, chlorantraniliprole,chlorazifop, chlorazifop-propargyl, chlorazine, chlorbenside,chlorbenzuron, chlorbicyclen, chlorbromuron, chlorbufam, chlordane,chlordecone, chlordimeform, chlordimeform hydrochloride,chlorempenthrin, chlorethoxyfos, chloreturon, chlorfenac,chlorfenac-ammonium, chlorfenac-sodium, chlorfenapyr, chlorfenazole,chlorfenethol, chlorfenprop, chlorfenson, chlorfensulphide,chlorfenvinphos, chlorfluazuron, chlorflurazole, chlorfluren,chlorfluren-methyl, chlorflurenol, chlorflurenol-methyl, chloridazon,chlorimuron, chlorimuron-ethyl, chlormephos, chlormequat, chlormequatchloride, chlornidine, chlornitrofen, chlorobenzilate,chlorodinitronaphthalenes, chloroform, chloromebuform, chloromethiuron,chloroneb, chlorophacinone, chlorophacinone-sodium, chloropicrin,chloropon, chloropropylate, chlorothalonil, chlorotoluron, chloroxuron,chloroxynil, chlorphonium, chlorphonium chloride, chlorphoxim,chlorprazophos, chlorprocarb, chlorpropham, chlorpyrifos,chlorpyrifos-methyl, chlorquinox, chlorsulfuron, chlorthal,chlorthal-dimethyl, chlorthal-monomethyl, chlorthiamid, chlorthiophos,chlozolinate, choline chloride, chromafenozide, cinerin I, cinerin II,cinerins, cinidon-ethyl, cinmethylin, cinosulfuron, ciobutide,cisanilide, cismethrin, clethodim, climbazole, cliodinate, clodinafop,clodinafop-propargyl, cloethocarb, clofencet, clofencet-potassium,clofentezine, clofibric acid, clofop, clofop-isobutyl, clomazone,clomeprop, cloprop, cloproxydim, clopyralid, clopyralid-methyl,clopyralid-olamine, clopyralid-potassium,clopyralid-tris(2-hydroxypropyl)ammonium, cloquintocet,cloquintocet-mexyl, cloransulam, cloransulam-methyl, closantel,clothianidin, clotrimazole, cloxyfonac, cloxyfonac-sodium, CMA,codlelure, colophonate, copper acetate, copper acetoarsenite, copperarsenate, copper carbonate, basic, copper hydroxide, copper naphthenate,copper oleate, copper oxychloride, copper silicate, copper sulfate,copper zinc chromate, coumachlor, coumafuryl, coumaphos, coumatetralyl,coumithoate, coumoxystrobin, CPMC, CPMF, CPPC, credazine, cresol,crimidine, crotamiton, crotoxyphos, crufomate, cryolite, cue-lure,cufraneb, cumyluron, cuprobam, cuprous oxide, curcumenol, cyanamide,cyanatryn, cyanazine, cyanofenphos, cyanophos, cyanthoate,cyantraniliprole, cyazofamid, cybutryne, cyclafuramid, cyclanilide,cyclethrin, cycloate, cycloheximide, cycloprate, cycloprothrin,cyclosulfamuron, cycloxydim, cycluron, cyenopyrafen, cyflufenamid,cyflumetofen, cyfluthrin, cyhalofop, cyhalofop-butyl, cyhalothrin,cyhexatin, cymiazole, cymiazole hydrochloride, cymoxanil, cyometrinil,cypendazole, cypermethrin, cyperquat, cyperquat chloride, cyphenothrin,cyprazine, cyprazole, cyproconazole, cyprodinil, cyprofuram, cypromid,cyprosulfamide, cyromazine, cythioate, daimuron, dalapon,dalapon-calcium, dalapon-magnesium, dalapon-sodium, daminozide,dayoutong, dazomet, dazomet-sodium, DBCP, d-camphor, DCIP, DCPTA, DDT,debacarb, decafentin, decarbofuran, dehydroacetic acid, delachlor,deltamethrin, demephion, demephion-O, demephion-S, demeton,demeton-methyl, demeton-O, demeton-O-methyl, demeton-S,demeton-S-methyl, demeton-S-methylsulphon, desmedipham, desmetryn,d-fanshiluquebingjuzhi, diafenthiuron, dialifos, di-allate, diamidafos,diatomaceous earth, diazinon, dibutyl phthalate, dibutyl succinate,dicamba, dicamba-diglycolamine, dicamba-dimethylammonium,dicamba-diolamine, dicamba-isopropylammonium, dicamba-methyl,dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-trolamine,dicapthon, dichlobenil, dichlofenthion, dichlofluanid, dichlone,dichloralurea, dichlorbenzuron, dichlorflurenol, dichlorflurenol-methyl,dichlormate, dichlormid, dichlorophen, dichlorprop,dichlorprop-2-ethylhexyl, dichlorprop-butotyl,dichlorprop-dimethylammonium, dichlorprop-ethylammonium,dichlorprop-isoctyl, dichlorprop-methyl, dichlorprop-P,dichlorprop-P-2-ethylhexyl, dichlorprop-P-dimethylammonium,dichlorprop-potassium, dichlorprop-sodium, dichlorvos, dichlozoline,diclobutrazol, diclocymet, diclofop, diclofop-methyl, diclomezine,diclomezine-sodium, dicloran, diclosulam, dicofol, dicoumarol, dicresyl,dicrotophos, dicyclanil, dicyclonon, dieldrin, dienochlor, diethamquat,diethamquat dichloride, diethatyl, diethatyl-ethyl, diethofencarb,dietholate, diethyl pyrocarbonate, diethyltoluamide, difenacoum,difenoconazole, difenopenten, difenopenten-ethyl, difenoxuron,difenzoquat, difenzoquat metilsulfate, difethialone, diflovidazin,diflubenzuron, diflufenican, diflufenzopyr, diflufenzopyr-sodium,diflumetorim, dikegulac, dikegulac-sodium, dilor, dimatif, dimefluthrin,dimefox, dimefuron, dimepiperate, dimetachlone, dimetan, dimethacarb,dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin,dimethirimol, dimethoate, dimethomorph, dimethrin, dimethyl carbate,dimethyl phthalate, dimethylvinphos, dimetilan, dimexano, dimidazon,dimoxystrobin, dinex, dinex-diclexine, dingjunezuo, diniconazole,diniconazole-M, dinitramine, dinobuton, dinocap, dinocap-4, dinocap-6,dinocton, dinofenate, dinopenton, dinoprop, dinosam, dinoseb, dinosebacetate, dinoseb-ammonium, dinoseb-diolamine, dinoseb-sodium,dinoseb-trolamine, dinosulfon, dinotefuran, dinoterb, dinoterb acetate,dinoterbon, diofenolan, dioxabenzofos, dioxacarb, dioxathion,diphacinone, diphacinone-sodium, diphenamid, diphenyl sulfone,diphenylamine, dipropalin, dipropetryn, dipyrithione, diquat, diquatdibromide, disparlure, disul, disulfiram, disulfoton, disul-sodium,ditalimfos, dithianon, dithicrofos, dithioether, dithiopyr, diuron,d-limonene, DMPA, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium,dodemorph, dodemorph acetate, dodemorph benzoate, dodicin, dodicinhydrochloride, dodicin-sodium, dodine, dofenapyn, dominicalure,doramectin, drazoxolon, DSMA, dufulin, EBEP, EBP, ecdysterone,edifenphos, eglinazine, eglinazine-ethyl, emamectin, emamectin benzoate,EMPC, empenthrin, endosulfan, endothal, endothal-diammonium,endothal-dipotassium, endothal-disodium, endothion, endrin,enestroburin, EPN, epocholeone, epofenonane, epoxiconazole,eprinomectin, epronaz, EPTC, erbon, ergocalciferol, erlujixiancaoan,esdépalléthrine, esfenvalerate, esprocarb, etacelasil, etaconazole,etaphos, etem, ethaboxam, ethachlor, ethalfluralin, ethametsulfuron,ethametsulfuron-methyl, ethaprochlor, ethephon, ethidimuron,ethiofencarb, ethiolate, ethion, ethiozin, ethiprole, ethirimol,ethoate-methyl, ethofumesate, ethohexadiol, ethoprophos, ethoxyfen,ethoxyfen-ethyl, ethoxyquin, ethoxysulfuron, ethychlozate, ethylformate, ethyl α-naphthaleneacetate, ethyl-DDD, ethylene, ethylenedibromide, ethylene dichloride, ethylene oxide, ethylicin, ethylmercury2,3-dihydroxypropyl mercaptide, ethylmercury acetate, ethylmercurybromide, ethylmercury chloride, ethylmercury phosphate, etinofen,etnipromid, etobenzanid, etofenprox, etoxazole, etridiazole, etrimfos,eugenol, EXD, famoxadone, famphur, fenamidone, fenaminosulf, fenamiphos,fenapanil, fenarimol, fenasulam, fenazaflor, fenazaquin, fenbuconazole,fenbutatin oxide, fenchlorazole, fenchlorazole-ethyl, fenchlorphos,fenclorim, fenethacarb, fenfluthrin, fenfuram, fenhexamid, fenitropan,fenitrothion, fenjuntong, fenobucarb, fenoprop, fenoprop-3-butoxypropyl,fenoprop-butometyl, fenoprop-butotyl, fenoprop-butyl, fenoprop-isoctyl,fenoprop-methyl, fenoprop-potassium, fenothiocarb, fenoxacrim,fenoxanil, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P,fenoxaprop-P-ethyl, fenoxasulfone, fenoxycarb, fenpiclonil,fenpirithrin, fenpropathrin, fenpropidin, fenpropimorph, fenpyrazamine,fenpyroximate, fenridazon, fenridazon-potassium, fenridazon-propyl,fenson, fensulfothion, fenteracol, fenthiaprop, fenthiaprop-ethyl,fenthion, fenthion-ethyl, fentin, fentin acetate, fentin chloride,fentin hydroxide, fentrazamide, fentrifanil, fenuron, fenuron TCA,fenvalerate, ferbam, ferimzone, ferrous sulfate, fipronil, flamprop,flamprop-isopropyl, flamprop-M, flamprop-methyl, flamprop-M-isopropyl,flamprop-M-methyl, flazasulfuron, flocoumafen, flonicamid, florasulam,fluacrypyrim, fluazifop, fluazifop-butyl, fluazifop-methyl, fluazifop-P,fluazifop-P-butyl, fluazinam, fluazolate, fluazuron, flubendiamide,flubenzimine, flucarbazone, flucarbazone-sodium, flucetosulfuron,fluchloralin, flucofuron, flucycloxuron, flucythrinate, fludioxonil,fluenetil, fluensulfone, flufenacet, flufenerim, flufenican,flufenoxuron, flufenprox, flufenpyr, flufenpyr-ethyl, flufiprole,flumethrin, flumetover, flumetralin, flumetsulam, flumezin, flumiclorac,flumiclorac-pentyl, flumioxazin, flumipropyn, flumorph, fluometuron,fluopicolide, fluopyram, fluorbenside, fluoridamid, fluoroacetamide,fluorodifen, fluoroglycofen, fluoroglycofen-ethyl, fluoroimide,fluoromidine, fluoronitrofen, fluothiuron, fluotrimazole, fluoxastrobin,flupoxam, flupropacil, flupropadine, flupropanate, flupropanate-sodium,flupyrsulfuron, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium,fluquinconazole, flurazole, flurenol, flurenol-butyl, flurenol-methyl,fluridone, flurochloridone, fluroxypyr, fluroxypyr-butometyl,fluroxypyr-meptyl, flurprimidol, flursulamid, flurtamone, flusilazole,flusulfamide, fluthiacet, fluthiacet-methyl, flutianil, flutolanil,flutriafol, fluvalinate, fluxapyroxad, fluxofenim, folpet, fomesafen,fomesafen-sodium, fonofos, foramsulfuron, forchlorfenuron, formaldehyde,formetanate, formetanate hydrochloride, formothion, formparanate,formparanate hydrochloride, fosamine, fosamine-ammonium, fosetyl,fosetyl-aluminium, fosmethilan, fospirate, fosthiazate, fosthietan,frontalin, fuberidazole, fucaojing, fucaomi, funaihecaoling,fuphenthiourea, furalane, furalaxyl, furamethrin, furametpyr,furathiocarb, furcarbanil, furconazole, furconazole-cis, furethrin,furfural, furilazole, furmecyclox, furophanate, furyloxyfen,gamma-cyhalothrin, gamma-HCH, genit, gibberellic acid, gibberellins,gliftor, glufosinate, glufosinate-ammonium, glufosinate-P,glufosinate-P-ammonium, glufosinate-P-sodium, glyodin, glyoxime,glyphosate, glyphosate-diammonium, glyphosate-dimethylammonium,glyphosate-isopropylammonium, glyphosate-monoammonium,glyphosate-potassium, glyphosate-sesquisodium, glyphosate-trimesium,glyphosine, gossyplure, grandlure, griseofulvin, guazatine, guazatineacetates, halacrinate, halfenprox, halofenozide, halosafen,halosulfuron, halosulfuron-methyl, haloxydine, haloxyfop,haloxyfop-etotyl, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-etotyl,haloxyfop-P-methyl, haloxyfop-sodium, HCH, hemel, hempa, HEOD,heptachlor, heptenophos, heptopargil, heterophos, hexachloroacetone,hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole,hexaflumuron, hexaflurate, hexalure, hexamide, hexazinone, hexylthiofos,hexythiazox, HHDN, holosulf, huancaiwo, huangcaoling, huanjunzuo,hydramethylnon, hydrargaphen, hydrated lime, hydrogen cyanide,hydroprene, hymexazol, hyquincarb, IAA, IBA, icaridin, imazalil,imazalil nitrate, imazalil sulfate, imazamethabenz,imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic,imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin,imazaquin-ammonium, imazaquin-methyl, imazaquin-sodium, imazethapyr,imazethapyr-ammonium, imazosulfuron, imibenconazole, imicyafos,imidacloprid, imidaclothiz, iminoctadine, iminoctadine triacetate,iminoctadine trialbesilate, imiprothrin, inabenfide, indanofan,indaziflam, indoxacarb, inezin, iodobonil, iodocarb, iodomethane,iodosulfuron, iodosulfuron-methyl, iodosulfuron-methyl-sodium, ioxynil,ioxynil octanoate, ioxynil-lithium, ioxynil-sodium, ipazine, ipconazole,ipfencarbazone, iprobenfos, iprodione, iprovalicarb, iprymidam,ipsdienol, ipsenol, IPSP, isamidofos, isazofos, isobenzan, isocarbamid,isocarbophos, isocil, isodrin, isofenphos, isofenphos-methyl, isolan,isomethiozin, isonoruron, isopolinate, isoprocarb, isopropalin,isoprothiolane, isoproturon, isopyrazam, isopyrimol, isothioate,isotianil, isouron, isovaledione, isoxaben, isoxachlortole, isoxadifen,isoxadifen-ethyl, isoxaflutole, isoxapyrifop, isoxathion, ivermectin,izopamfos, japonilure, japothrins, jasmolin I, jasmolin II, jasmonicacid, jiahuangchongzong, jiajizengxiaolin, jiaxiangjunzhi, jiecaowan,jiecaoxi, jodfenphos, juvenile hormone I, juvenile hormone II, juvenilehormone III, kadethrin, karbutilate, karetazan, karetazan-potassium,kasugamycin, kasugamycin hydrochloride, kejunlin, kelevan, ketospiradox,ketospiradox-potassium, kinetin, kinoprene, kresoxim-methyl, kuicaoxi,lactofen, lambda-cyhalothrin, latilure, lead arsenate, lenacil,lepimectin, leptophos, lindane, lineatin, linuron, lirimfos, litlure,looplure, lufenuron, lvdingjunzhi, lvxiancaolin, lythidathion, MAA,malathion, maleic hydrazide, malonoben, maltodextrin, MAMA, mancopper,mancozeb, mandipropamid, maneb, matrine, mazidox, MCPA,MCPA-2-ethylhexyl, MCPA-butotyl, MCPA-butyl, MCPA-dimethylammonium,MCPA-diolamine, MCPA-ethyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl,MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium, MCPA-thioethyl,MCPA-trolamine, MCPB, MCPB-ethyl, MCPB-methyl, MCPB-sodium, mebenil,mecarbam, mecarbinzid, mecarphon, mecoprop, mecoprop-2-ethylhexyl,mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl,mecoprop-isoctyl, mecoprop-methyl, mecoprop-P, mecoprop-P-2-ethylhexyl,mecoprop-P-dimethylammonium, mecoprop-P-isobutyl, mecoprop-potassium,mecoprop-P-potassium, mecoprop-sodium, mecoprop-trolamine, medimeform,medinoterb, medinoterb acetate, medlure, mefenacet, mefenpyr,mefenpyr-diethyl, mefluidide, mefluidide-diolamine,mefluidide-potassium, megatomoic acid, menazon, mepanipyrim,meperfluthrin, mephenate, mephosfolan, mepiquat, mepiquat chloride,mepiquat pentaborate, mepronil, meptyldinocap, mercuric chloride,mercuric oxide, mercurous chloride, merphos, mesoprazine, mesosulfuron,mesosulfuron-methyl, mesotrione, mesulfen, mesulfenfos, metaflumizone,metalaxyl, metalaxyl-M, metaldehyde, metam, metam-ammonium, metamifop,metamitron, metam-potassium, metam-sodium, metazachlor, metazosulfuron,metazoxolon, metconazole, metepa, metflurazon, methabenzthiazuron,methacrifos, methalpropalin, methamidophos, methasulfocarb, methazole,methfuroxam, methidathion, methiobencarb, methiocarb,methiopyrisulfuron, methiotepa, methiozolin, methiuron, methocrotophos,methometon, methomyl, methoprene, methoprotryne, methoquin-butyl,methothrin, methoxychlor, methoxyfenozide, methoxyphenone, methylapholate, methyl bromide, methyl eugenol, methyl iodide, methylisothiocyanate, methylacetophos, methylchloroform, methyldymron,methylene chloride, methylmercury benzoate, methylmercury dicyandiamide,methylmercury pentachlorophenoxide, methylneodecanamide, metiram,metobenzuron, metobromuron, metofluthrin, metolachlor, metolcarb,metominostrobin, metosulam, metoxadiazone, metoxuron, metrafenone,metribuzin, metsulfovax, metsulfuron, metsulfuron-methyl, mevinphos,mexacarbate, mieshuan, milbemectin, milbemycin oxime, milneb, mipafox,mirex, MNAF, moguchun, molinate, molosultap, monalide, monisouron,monochloroacetic acid, monocrotophos, monolinuron, monosulfuron,monosulfuron-ester, monuron, monuron TCA, morfamquat, morfamquatdichloride, moroxydine, moroxydine hydrochloride, morphothion, morzid,moxidectin, MSMA, muscalure, myclobutanil, myclozolin,N-(ethylmercury)-p-toluenesulphonanilide, nabam, naftalofos, naled,naphthalene, naphthaleneacetamide, naphthalic anhydride, naphthoxyaceticacids, naproanilide, napropamide, naptalam, naptalam-sodium, natamycin,neburon, niclosamide, niclosamide-olamine, nicosulfuron, nicotine,nifluridide, nipyraclofen, nitenpyram, nithiazine, nitralin, nitrapyrin,nitrilacarb, nitrofen, nitrofluorfen, nitrostyrene, nitrothal-isopropyl,norbormide, norflurazon, nornicotine, noruron, novaluron, noviflumuron,nuarimol, OCH, octachlorodipropyl ether, octhilinone, ofurace,omethoate, orbencarb, orfralure, ortho-dichlorobenzene, orthosulfamuron,oryctalure, orysastrobin, oryzalin, osthol, ostramone, oxabetrinil,oxadiargyl, oxadiazon, oxadixyl, oxamate, oxamyl, oxapyrazon,oxapyrazon-dimolamine, oxapyrazon-sodium, oxasulfuron, oxaziclomefone,oxine-copper, oxolinic acid, oxpoconazole, oxpoconazole fumarate,oxycarboxin, oxydemeton-methyl, oxydeprofos, oxydisulfoton, oxyfluorfen,oxymatrine, oxytetracycline, oxytetracycline hydrochloride,paclobutrazol, paichongding, para-dichlorobenzene, parafluron, paraquat,paraquat dichloride, paraquat dimetilsulfate, parathion,parathion-methyl, parinol, pebulate, pefurazoate, pelargonic acid,penconazole, pencycuron, pendimethalin, penflufen, penfluron,penoxsulam, pentachlorophenol, pentanochlor, penthiopyrad, pentmethrin,pentoxazone, perfluidone, permethrin, pethoxamid, phenamacril, phenazineoxide, phenisopham, phenkapton, phenmedipham, phenmedipham-ethyl,phenobenzuron, phenothrin, phenproxide, phenthoate, phenylmercuriurea,phenylmercury acetate, phenylmercury chloride, phenylmercury derivativeof pyrocatechol, phenylmercury nitrate, phenylmercury salicylate,phorate, phosacetim, phosalone, phosdiphen, phosfolan, phosfolan-methyl,phosglycin, phosmet, phosnichlor, phosphamidon, phosphine, phosphocarb,phosphorus, phostin, phoxim, phoxim-methyl, phthalide, picloram,picloram-2-ethylhexyl, picloram-isoctyl, picloram-methyl,picloram-olamine, picloram-potassium, picloram-triethylammonium,picloram-tris(2-hydroxypropyl)ammonium, picolinafen, picoxystrobin,pindone, pindone-sodium, pinoxaden, piperalin, piperonyl butoxide,piperonyl cyclonene, piperophos, piproctanyl, piproctanyl bromide,piprotal, pirimetaphos, pirimicarb, pirimioxyphos, pirimiphos-ethyl,pirimiphos-methyl, plifenate, polycarbamate, polyoxins, polyoxorim,polyoxorim-zinc, polythialan, potassium arsenite, potassium azide,potassium cyanate, potassium gibberellate, potassium naphthenate,potassium polysulfide, potassium thiocyanate, potassiumα-naphthaleneacetate, pp′-DDT, prallethrin, precocene I, precocene II,precocene III, pretilachlor, primidophos, primisulfuron,primisulfuron-methyl, probenazole, prochloraz, prochloraz-manganese,proclonol, procyazine, procymidone, prodiamine, profenofos, profluazol,profluralin, profluthrin, profoxydim, proglinazine, proglinazine-ethyl,prohexadione, prohexadione-calcium, prohydrojasmon, promacyl, promecarb,prometon, prometryn, promurit, propachlor, propamidine, propamidinedihydrochloride, propamocarb, propamocarb hydrochloride, propanil,propaphos, propaquizafop, propargite, proparthrin, propazine,propetamphos, propham, propiconazole, propineb, propisochlor, propoxur,propoxycarbazone, propoxycarbazone-sodium, propyl isome,propyrisulfuron, propyzamide, proquinazid, prosuler, prosulfalin,prosulfocarb, prosulfuron, prothidathion, prothiocarb, prothiocarbhydrochloride, prothioconazole, prothiofos, prothoate, protrifenbute,proxan, proxan-sodium, prynachlor, pydanon, pymetrozine, pyracarbolid,pyraclofos, pyraclonil, pyraclostrobin, pyraflufen, pyraflufen-ethyl,pyrafluprole, pyramat, pyrametostrobin, pyraoxystrobin, pyrasulfotole,pyrazolynate, pyrazophos, pyrazosulfuron, pyrazosulfuron-ethyl,pyrazothion, pyrazoxyfen, pyresmethrin, pyrethrin I, pyrethrin II,pyrethrins, pyribambenz-isopropyl, pyribambenz-propyl, pyribencarb,pyribenzoxim, pyributicarb, pyriclor, pyridaben, pyridafol, pyridalyl,pyridaphenthion, pyridate, pyridinitril, pyrifenox, pyrifluquinazon,pyriftalid, pyrimethanil, pyrimidifen, pyriminobac, pyriminobac-methyl,pyrimisulfan, pyrimitate, pyrinuron, pyriofenone, pyriprole,pyripropanol, pyriproxyfen, pyrithiobac, pyrithiobac-sodium, pyrolan,pyroquilon, pyroxasulfone, pyroxsulam, pyroxychlor, pyroxyfur, quassia,quinacetol, quinacetol sulfate, quinalphos, quinalphos-methyl,quinazamid, quinclorac, quinconazole, quinmerac, quinoclamine,quinonamid, quinothion, quinoxyfen, quintiofos, quintozene, quizalofop,quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl,quizalofop-P-tefuryl, quwenzhi, quyingding, rabenzazole, rafoxanide,rebemide, resmethrin, rhodethanil, rhodojaponin-III, ribavirin,rimsulfuron, rotenone, ryania, saflufenacil, saijunmao, saisentong,salicylanilide, sanguinarine, santonin, schradan, scilliroside,sebuthylazine, secbumeton, sedaxane, selamectin, semiamitraz,semiamitraz chloride, sesamex, sesamolin, sethoxydim, shuangjiaancaolin,siduron, siglure, silafluofen, silatrane, silica gel, silthiofam,simazine, simeconazole, simeton, simetryn, sintofen, SMA, S-metolachlor,sodium arsenite, sodium azide, sodium chlorate, sodium fluoride, sodiumfluoroacetate, sodium hexafluorosilicate, sodium naphthenate, sodiumorthophenylphenoxide, sodium pentachlorophenoxide, sodium polysulfide,sodium thiocyanate, sodium α-naphthaleneacetate, sophamide, spinetoram,spinosad, spirodiclofen, spiromesifen, spirotetramat, spiroxamine,streptomycin, streptomycin sesquisulfate, strychnine, sulcatol,sulcofuron, sulcofuron-sodium, sulcotrione, sulfallate, sulfentrazone,sulfiram, sulfluramid, sulfometuron, sulfometuron-methyl, sulfosulfuron,sulfotep, sulfoxaflor, sulfoxide, sulfoxime, sulfur, sulfuric acid,sulfuryl fluoride, sulglycapin, sulprofos, sultropen, swep,tau-fluvalinate, tavron, tazimcarb, TCA, TCA-ammonium, TCA-calcium,TCA-ethadyl, TCA-magnesium, TCA-sodium, TDE, tebuconazole, tebufenozide,tebufenpyrad, tebufloquin, tebupirimfos, tebutam, tebuthiuron,tecloftalam, tecnazene, tecoram, teflubenzuron, tefluthrin,tefuryltrione, tembotrione, temephos, tepa, TEPP, tepraloxydim,terallethrin, terbacil, terbucarb, terbuchlor, terbufos, terbumeton,terbuthylazine, terbutryn, tetcyclacis, tetrachloroethane,tetrachlorvinphos, tetraconazole, tetradifon, tetrafluron, tetramethrin,tetramethylfluthrin, tetramine, tetranactin, tetrasul, thallium sulfate,thenylchlor, theta-cypermethrin, thiabendazole, thiacloprid,thiadifluor, thiamethoxam, thiapronil, thiazafluron, thiazopyr,thicrofos, thicyofen, thidiazimin, thidiazuron, thiencarbazone,thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl,thifluzamide, thiobencarb, thiocarboxime, thiochlorfenphim, thiocyclam,thiocyclam hydrochloride, thiocyclam oxalate, thiodiazole-copper,thiodicarb, thiofanox, thiofluoximate, thiohempa, thiomersal, thiometon,thionazin, thiophanate, thiophanate-methyl, thioquinox,thiosemicarbazide, thiosultap, thiosultap-diammonium,thiosultap-disodium, thiosultap-monosodium, thiotepa, thiram,thuringiensin, tiadinil, tiaojiean, tiocarbazil, tioclorim, tioxymid,tirpate, tolclofos-methyl, tolfenpyrad, tolylfluanid, tolylmercuryacetate, topramezone, tralkoxydim, tralocythrin, tralomethrin,tralopyril, transfluthrin, transpermethrin, tretamine, triacontanol,triadimefon, triadimenol, triafamone, tri-allate, triamiphos,triapenthenol, triarathene, triarimol, triasulfuron, triazamate,triazbutil, triaziflam, triazophos, triazoxide, tribenuron,tribenuron-methyl, tribufos, tributyltin oxide, tricamba, trichlamide,trichlorfon, trichlormetaphos-3, trichloronat, triclopyr,triclopyr-butotyl, triclopyr-ethyl, triclopyr-triethylammonium,tricyclazole, tridemorph, tridiphane, trietazine, trifenmorph,trifenofos, trifloxystrobin, trifloxysulfuron, trifloxysulfuron-sodium,triflumizole, triflumuron, trifluralin, triflusulfuron,triflusulfuron-methyl, trifop, trifop-methyl, trifopsime, triforine,trihydroxytriazine, trimedlure, trimethacarb, trimeturon, trinexapac,trinexapac-ethyl, triprene, tripropindan, triptolide, tritac,triticonazole, tritosulfuron, trunc-call, uniconazole, uniconazole-P,urbacide, uredepa, valerate, validamycin, valifenalate, valone,vamidothion, vangard, vaniliprole, vernolate, vinclozolin, warfarin,warfarin-potassium, warfarin-sodium, xiaochongliulin, xinjunan,xiwojunan, XMC, xylachlor, xylenols, xylylcarb, yishijing, zarilamid,zeatin, zengxiaoan, zeta-cypermethrin, zinc naphthenate, zinc phosphide,zinc thiazole, zineb, ziram, zolaprofos, zoxamide, zuomihuanglong,α-chlorohydrin, α-ecdysone, α-multistriatin, and α-naphthaleneaceticacid. For more information consult the “COMPENDIUM OF PESTICIDE COMMONNAMES” located at http://www.alanwood.net/pesticides/index.html. Alsoconsult “THE PESTICIDE MANUAL” 14th Edition, edited by C D S Tomlin,copyright 2006 by British Crop Production Council, or its prior or morerecent editions.

Biopesticides

Compounds according to formula (I) may also be used in combination (suchas in a compositional mixture, or a simultaneous or sequentialapplication) with one or more biopesticides. The term “biopesticide” isused for microbial biological pest control agents that are applied in asimilar manner to chemical pesticides. Commonly these are bacterial, butthere are also examples of fungal control agents, including Trichodermaspp. and Ampelomyces quisqualis (a control agent for grape powderymildew). Bacillus subtilis are used to control plant pathogens. Weedsand rodents have also been controlled with microbial agents. Onewell-known insecticide example is Bacillus thuringiensis, a bacterialdisease of Lepidoptera, Coleoptera, and Diptera. Because it has littleeffect on other organisms, it is considered more environmentallyfriendly than synthetic pesticides. Biological insecticides includeproducts based on:

1. entomopathogenic fungi (e.g. Metarhizium anisopliae);

2. entomopathogenic nematodes (e.g. Steinernema feltiae); and

3. entomopathogenic viruses (e.g. Cydia pomonella granulovirus).

Other examples of entomopathogenic organisms include, but are notlimited to, baculoviruses, bacteria and other prokaryotic organisms,fungi, protozoa and Microsproridia. Biologically derived insecticidesinclude, but not limited to, rotenone, veratridine, as well as microbialtoxins; insect tolerant or resistant plant varieties; and organismsmodified by recombinant DNA technology to either produce insecticides orto convey an insect resistant property to the genetically modifiedorganism. In one embodiment, compounds according to formula (I) may beused with one or more biopesticides in the area of seed treatments andsoil amendments. The Manual of Biocontrol Agents gives a review of theavailable biological insecticide (and other biology-based control)products. Copping L. G. (ed.) (2004). The Manual of Biocontrol Agents(formerly the Biopesticide Manual) 3rd Edition. British Crop ProductionCouncil (BCPC), Farnham, Surrey UK.

Other Active Compounds

Compounds according to formula (I) may also be used in combination (suchas in a compositional mixture, or a simultaneous or sequentialapplication) with one or more of the following:

-   1.    3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-oxa-1-azaspiro[4,5]dec-3-en-2-one;-   2.    3-(4′-chloro-2,4-dimethyl[1,1′-biphenyl]-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4,5]dec-3-en-2-one;-   3. 4-[[(6-chloro-3-pyridinyl)methyl]methylamino]-2(5H)-furanone;-   4.    4-[[(6-chloro-3-pyridinyl)methyl]cyclopropylamino]-2(5H)-furanone;-   5.    3-chloro-N2-[(15)-1-methyl-2-(methylsulfonyl)ethyl]-N1-[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-1,2-benzenedicarboxamide;-   6. 2-cyano-N-ethyl-4-fluoro-3-methoxy-benenesulfonamide;-   7. 2-cyano-N-ethyl-3-methoxy-benzenesulfonamide;-   8. 2-cyano-3-difluoromethoxy-N-ethyl-4-fluoro-benzenesulfonamide;-   9. 2-cyano-3-fluoromethoxy-N-ethyl-benzenesulfonamide;-   10. 2-cyano-6-fluoro-3-methoxy-N,N-dimethyl-benzenesulfonamide;-   11. 2-cyano-N-ethyl-6-fluoro-3-methoxy-N-methyl-benzenesulfonamide;-   12. 2-cyano-3-difluoromethoxy-N,N-dimethylbenzenesulfon-amide;-   13.    3-(difluoromethyl)-N-[2-(3,3-dimethylbutyl)phenyl]-1-methyl-1H-pyrazole-4-carboxamide;-   14.    N-ethyl-2,2-dimethylpropionamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)hydrazone;-   15.    N-ethyl-2,2-dichloro-1-methylcyclopropane-carboxamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)hydrazone    nicotine;-   16.    O-{(E-)-[2-(4-chloro-phenyl)-2-cyano-1-(2-trifluoromethylphenyl)-vinyl]}S-methyl    thiocarbonate;-   17.    (E)-N1-[(2-chloro-1,3-thiazol-5-ylmethyl)]-N2-cyano-N1-methylacetamidine;-   18.    1-(6-chloropyridin-3-ylmethyl)-7-methyl-8-nitro-1,2,3,5,6,7-hexahydro-imidazo[1,2-a]pyridin-5-ol;-   19. 4-[4-chlorophenyl-(2-butylidine-hydrazono)methyl)]phenyl    mesylate; and-   20.    N-Ethyl-2,2-dichloro-1-methylcyclopropanecarboxamide-2-(2,6-dichloro-alpha,alpha,alpha-trifluoro-p-tolyl)hydrazone.

Synergistic Mixtures

Compounds according to formula (I) may be used with certain activecompounds to form synergistic mixtures where the mode of action of suchcompounds compared to the mode of action of compounds according toformula (I) are the same, similar, or different. Examples of modes ofaction include, but are not limited to: acetylcholinesterase inhibitor;sodium channel modulator; chitin biosynthesis inhibitor; GABA andglutamate-gated chloride channel antagonist; GABA and glutamate-gatedchloride channel agonist; acetylcholine receptor agonist; acetylcholinereceptor antagonist; MET I inhibitor; Mg-stimulated ATPase inhibitor;nicotinic acetylcholine receptor; Midgut membrane disrupter; oxidativephosphorylation disrupter, and ryanodine receptor (RyRs). Generally,weight ratios of compounds according to formula (I) in a synergisticmixture with another compound are from about 10:1 to about 1:10, inanother embodiment from about 5:1 to about 1:5, and in anotherembodiment from about 3:1, and in another embodiment about 1:1.

Formulations

A pesticide may not suitable for application in its pure form. It may benecessary to add other substances so that the pesticide can be used atthe required concentration and in an appropriate form, permitting easeof application, handling, transportation, storage, and maximum pesticideactivity. Thus, pesticides can be formulated into, for example, baits,concentrated emulsions, dusts, emulsifiable concentrates, fumigants,gels, granules, microencapsulations, seed treatments, suspensionconcentrates, suspoemulsions, tablets, water soluble liquids, waterdispersible granules or dry flowables, wettable powders, and ultra lowvolume solutions. For further information on formulation types see“Catalogue of Pesticide Formulation Types and International CodingSystem” Technical Monograph n^(o) 2, 5th Edition by CropLifeInternational (2002).

Pesticides are applied most often as aqueous suspensions or emulsionsprepared from concentrated formulations of such pesticides. Suchwater-soluble, water-suspendable, or emulsifiable formulations areeither solids, usually known as wettable powders, or water dispersiblegranules, or liquids usually known as emulsifiable concentrates, oraqueous suspensions. Wettable powders, which may be compacted to formwater dispersible granules, comprise an intimate mixture of thepesticide, a carrier, and surfactants. The concentration of thepesticide is usually from about 10% to about 90% by weight. The carrieris usually selected from among the attapulgite clays, themontmorillonite clays, the diatomaceous earths, or the purifiedsilicates. Effective surfactants, comprising from about 0.5% to about10% of the wettable powder, are found among sulfonated lignins,condensed naphthalenesulfonates, naphthalenesulfonates,alkylbenzenesulfonates, alkyl sulfates, and non-ionic surfactants suchas ethylene oxide adducts of alkyl phenols.

Emulsifiable concentrates of pesticides comprise a convenientconcentration of a pesticide, such as from about 50 to about 500 gramsper liter of liquid dissolved in a carrier that is either a watermiscible solvent or a mixture of water-immiscible organic solvent andemulsifiers. Useful organic solvents include aromatics, especiallyxylenes and petroleum fractions, especially the high-boilingnaphthalenic and olefinic portions of petroleum such as heavy aromaticnaphtha. Other organic solvents may also be used, such as the terpenicsolvents including rosin derivatives, aliphatic ketones such ascyclohexanone, and complex alcohols such as 2-ethoxyethanol. Suitableemulsifiers for emulsifiable concentrates are selected from conventionalanionic and non-ionic surfactants.

Aqueous suspensions comprise suspensions of water-insoluble pesticidesdispersed in an aqueous carrier at a concentration in the range fromabout 5% to about 50% by weight. Suspensions are prepared by finelygrinding the pesticide and vigorously mixing it into a carrier comprisedof water and surfactants. Ingredients, such as inorganic salts andsynthetic or natural gums may also be added, to increase the density andviscosity of the aqueous carrier. It is often most effective to grindand mix the pesticide at the same time by preparing the aqueous mixtureand homogenizing it in an implement such as a sand mill, ball mill, orpiston-type homogenizer.

Pesticides may also be applied as granular compositions that areparticularly useful for applications to the soil. Granular compositionsusually contain from about 0.5% to about 10% by weight of the pesticide,dispersed in a carrier that comprises clay or a similar substance. Suchcompositions are usually prepared by dissolving the pesticide in asuitable solvent and applying it to a granular carrier which has beenpre-formed to the appropriate particle size, in the range of from about0.5 to about 3 mm. Such compositions may also be formulated by making adough or paste of the carrier and compound and crushing and drying toobtain the desired granular particle size.

Dusts containing a pesticide are prepared by intimately mixing thepesticide in powdered form with a suitable dusty agricultural carrier,such as kaolin clay, ground volcanic rock, and the like. Dusts cansuitably contain from about 1% to about 10% of the pesticide. They canbe applied as a seed dressing or as a foliage application with a dustblower machine.

It is equally practical to apply a pesticide in the form of a solutionin an appropriate organic solvent, usually petroleum oil, such as thespray oils, which are widely used in agricultural chemistry.

Pesticides can also be applied in the form of an aerosol composition. Insuch compositions the pesticide is dissolved or dispersed in a carrier,which is a pressure-generating propellant mixture. The aerosolcomposition is packaged in a container from which the mixture isdispensed through an atomizing valve.

Pesticide baits are formed when the pesticide is mixed with food or anattractant or both. When the pests eat the bait they also consume thepesticide. Baits may take the form of granules, gels, flowable powders,liquids, or solids. They can be used in pest harborages.

Fumigants are pesticides that have a relatively high vapor pressure andhence can exist as a gas in sufficient concentrations to kill pests insoil or enclosed spaces. The toxicity of the fumigant is proportional toits concentration and the exposure time. They are characterized by agood capacity for diffusion and act by penetrating the pest'srespiratory system or being absorbed through the pest's cuticle.Fumigants are applied to control stored product pests under gas proofsheets, in gas sealed rooms or buildings or in special chambers.

Pesticides can be microencapsulated by suspending the pesticideparticles or droplets in plastic polymers of various types. By alteringthe chemistry of the polymer or by changing factors in the processing,microcapsules can be formed of various sizes, solubility, wallthicknesses, and degrees of penetrability. These factors govern thespeed with which the active ingredient within is released, which inturn, affects the residual performance, speed of action, and odor of theproduct.

Oil solution concentrates are made by dissolving pesticide in a solventthat will hold the pesticide in solution. Oil solutions of a pesticideusually provide faster knockdown and kill of pests than otherformulations due to the solvents themselves having pesticidal action andthe dissolution of the waxy covering of the integument increasing thespeed of uptake of the pesticide. Other advantages of oil solutionsinclude better storage stability, better penetration of crevices, andbetter adhesion to greasy surfaces.

Another embodiment is an oil-in-water emulsion, wherein the emulsioncomprises oily globules which are each provided with a lamellar liquidcrystal coating and are dispersed in an aqueous phase, wherein each oilyglobule comprises at least one compound which is agriculturally active,and is individually coated with a monolamellar or oligolamellar layercomprising: (1) at least one non-ionic lipophilic surface-active agent,(2) at least one non-ionic hydrophilic surface-active agent and (3) atleast one ionic surface-active agent, wherein the globules having a meanparticle diameter of less than 800 nanometers. Further information onthe embodiment is disclosed in U.S. patent publication No. 20070027034published Feb. 1, 2007, having patent application Ser. No. 11/495,228.For ease of use, this embodiment will be referred to as “OIWE”.

For further information consult “Insect Pest Management” 2nd Edition byD. Dent, copyright CAB International (2000). Additionally, for moredetailed information consult “Handbook of Pest Control—The Behavior,Life History, and Control of Household Pests” by Arnold Mallis, 9thEdition, copyright 2004 by GIE Media Inc.

Other Formulation Components

Generally, when the compounds disclosed herein are used in aformulation, such formulation can also contain other components. Thesecomponents include, but are not limited to, (this is a non-exhaustiveand non-mutually exclusive list) wetters, spreaders, stickers,penetrants, buffers, sequestering agents, drift reduction agents,compatibility agents, anti-foam agents, cleaning agents, andemulsifiers. A few components are described forthwith.

A wetting agent is a substance that when added to a liquid increases thespreading or penetration power of the liquid by reducing the interfacialtension between the liquid and the surface on which it is spreading.Wetting agents are used for two main functions in agrochemicalformulations: during processing and manufacture to increase the rate ofwetting of powders in water to make concentrates for soluble liquids orsuspension concentrates; and during mixing of a product with water in aspray tank to reduce the wetting time of wettable powders and to improvethe penetration of water into water-dispersible granules. Examples ofwetting agents used in wettable powder, suspension concentrate, andwater-dispersible granule formulations are: sodium lauryl sulfate;sodium dioctyl sulfosuccinate; alkyl phenol ethoxylates; and aliphaticalcohol ethoxylates.

A dispersing agent is a substance which adsorbs onto the surface ofparticles and helps to preserve the state of dispersion of the particlesand prevents them from reaggregating. Dispersing agents are added toagrochemical formulations to facilitate dispersion and suspension duringmanufacture, and to ensure the particles redisperse into water in aspray tank. They are widely used in wettable powders, suspensionconcentrates and water-dispersible granules. Surfactants that are usedas dispersing agents have the ability to adsorb strongly onto a particlesurface and provide a charged or steric barrier to reaggregation ofparticles. The most commonly used surfactants are anionic, non-ionic, ormixtures of the two types. For wettable powder formulations, the mostcommon dispersing agents are sodium lignosulfonates. For suspensionconcentrates, very good adsorption and stabilization are obtained usingpolyelectrolytes, such as sodium naphthalene sulfonate formaldehydecondensates. Tristyrylphenol ethoxylate phosphate esters are also used.Non-ionics such as alkylarylethylene oxide condensates and EO-PO blockcopolymers are sometimes combined with anionics as dispersing agents forsuspension concentrates. In recent years, new types of very highmolecular weight polymeric surfactants have been developed as dispersingagents. These have very long hydrophobic ‘backbones’ and a large numberof ethylene oxide chains forming the ‘teeth’ of a ‘comb’ surfactant.These high molecular weight polymers can give very good long-termstability to suspension concentrates because the hydrophobic backboneshave many anchoring points onto the particle surfaces. Examples ofdispersing agents used in agrochemical formulations are: sodiumlignosulfonates; sodium naphthalene sulfonate formaldehyde condensates;tristyrylphenol ethoxylate phosphate esters; aliphatic alcoholethoxylates; alkyl ethoxylates; EO-PO block copolymers; and graftcopolymers.

An emulsifying agent is a substance which stabilizes a suspension ofdroplets of one liquid phase in another liquid phase. Without theemulsifying agent the two liquids would separate into two immiscibleliquid phases. The most commonly used emulsifier blends containalkylphenol or aliphatic alcohol with twelve or more ethylene oxideunits and the oil-soluble calcium salt of dodecylbenzenesulfonic acid. Arange of hydrophile-lipophile balance (“HLB”) values from 8 to 18 willnormally provide good stable emulsions. Emulsion stability can sometimesbe improved by the addition of a small amount of an EO-PO blockcopolymer surfactant.

A solubilizing agent is a surfactant which will form micelles in waterat concentrations above the critical micelle concentration. The micellesare then able to dissolve or solubilize water-insoluble materials insidethe hydrophobic part of the micelle. The types of surfactants usuallyused for solubilization are non-ionics, sorbitan monooleates, sorbitanmonooleate ethoxylates, and methyl oleate esters.

Surfactants are sometimes used, either alone or with other additivessuch as mineral or vegetable oils as adjuvants to spray-tank mixes toimprove the biological performance of the pesticide on the target. Thetypes of surfactants used for bioenhancement depend generally on thenature and mode of action of the pesticide. However, they are oftennon-ionics such as: alkyl ethoxylates; linear aliphatic alcoholethoxylates; aliphatic amine ethoxylates.

A carrier or diluent in an agricultural formulation is a material addedto the pesticide to give a product of the required strength. Carriersare usually materials with high absorptive capacities, while diluentsare usually materials with low absorptive capacities. Carriers anddiluents are used in the formulation of dusts, wettable powders,granules and water-dispersible granules.

Organic solvents are used mainly in the formulation of emulsifiableconcentrates, oil-in-water emulsions, suspoemulsions, and ultra lowvolume formulations, and to a lesser extent, granular formulations.Sometimes mixtures of solvents are used. The first main groups ofsolvents are aliphatic paraffinic oils such as kerosene or refinedparaffins. The second main group (and the most common) comprises thearomatic solvents such as xylene and higher molecular weight fractionsof C₉ and C₁₀ aromatic solvents. Chlorinated hydrocarbons are useful ascosolvents to prevent crystallization of pesticides when the formulationis emulsified into water. Alcohols are sometimes used as cosolvents toincrease solvent power. Other solvents may include vegetable oils, seedoils, and esters of vegetable and seed oils.

Thickeners or gelling agents are used mainly in the formulation ofsuspension concentrates, emulsions and suspoemulsions to modify therheology or flow properties of the liquid and to prevent separation andsettling of the dispersed particles or droplets. Thickening, gelling,and anti-settling agents generally fall into two categories, namelywater-insoluble particulates and water-soluble polymers. It is possibleto produce suspension concentrate formulations using clays and silicas.Examples of these types of materials, include, but are not limited to,montmorillonite, bentonite, magnesium aluminum silicate, andattapulgite. Water-soluble polysaccharides have been used asthickening-gelling agents for many years. The types of polysaccharidesmost commonly used are natural extracts of seeds and seaweeds or aresynthetic derivatives of cellulose. Examples of these types of materialsinclude, but are not limited to, guar gum; locust bean gum; carrageenam;alginates; methyl cellulose; sodium carboxymethyl cellulose (SCMC);hydroxyethyl cellulose (HEC). Other types of anti-settling agents arebased on modified starches, polyacrylates, polyvinyl alcohol andpolyethylene oxide. Another good anti-settling agent is xanthan gum.

Microorganisms can cause spoilage of formulated products. Thereforepreservation agents are used to eliminate or reduce their effect.Examples of such agents include, but are not limited to: propionic acidand its sodium salt; sorbic acid and its sodium or potassium salts;benzoic acid and its sodium salt; p-hydroxybenzoic acid sodium salt;methyl p-hydroxybenzoate; and 1,2-benzisothiazolin-3-one (BIT).

The presence of surfactants often causes water-based formulations tofoam during mixing operations in production and in application through aspray tank. In order to reduce the tendency to foam, anti-foam agentsare often added either during the production stage or before fillinginto bottles. Generally, there are two types of anti-foam agents, namelysilicones and non-silicones. Silicones are usually aqueous emulsions ofdimethyl polysiloxane, while the non-silicone anti-foam agents arewater-insoluble oils, such as octanol and nonanol, or silica. In bothcases, the function of the anti-foam agent is to displace the surfactantfrom the air-water interface.

“Green” agents (e.g., adjuvants, surfactants, solvents) can reduce theoverall environmental footprint of crop protection formulations. Greenagents are biodegradable and generally derived from natural and/orsustainable sources, e.g. plant and animal sources. Specific examplesare: vegetable oils, seed oils, and esters thereof, also alkoxylatedalkyl polyglucosides.

For further information, see “Chemistry and Technology of AgrochemicalFormulations” edited by D. A. Knowles, copyright 1998 by Kluwer AcademicPublishers. Also see “Insecticides in Agriculture andEnvironment—Retrospects and Prospects” by A. S. Perry, I. Yamamoto, I.Ishaaya, and R. Perry, copyright 1998 by Springer-Verlag.

Pests

In general, compounds according to formula (I) may be used to controlpests e.g. ants, aphids, beetles, bristletails, cockroaches, crickets,earwigs, fleas, flies, grasshoppers, leafhoppers, lice, locusts, mites,moths, nematodes, scales, symphylans, termites, thrips, ticks, wasps,and whiteflies.

In another embodiment, the compounds according to formula (I) may beused to control pests in the Phyla Nematoda and/or Arthropoda.

In another embodiment, the compounds according to formula (I) may beused to control pests in the Subphyla Chelicerata, Myriapoda, and/orHexapoda.

In another embodiment, the compounds according to formula (I) may beused to control pests in the Classes of Arachnida, Symphyla, and/orInsecta.

In another embodiment, the compounds according to formula (I) may beused to control pests of the Order Anoplura. A non-exhaustive list ofparticular genera includes, but is not limited to, Haematopinus spp.,Hoplopleura spp., Linognathus spp., Pediculus spp., and Polyplax spp. Anon-exhaustive list of particular species includes, but is not limitedto, Haematopinus asini, Haematopinus suis, Linognathus setosus,Linognathus ovillus, Pediculus humanus capitis, Pediculus humanushumanus, and Pthirus pubis.

In another embodiment, the compounds according to formula (I) may beused to control pests in the Order Coleoptera. A non-exhaustive list ofparticular genera includes, but is not limited to, Acanthoscelides spp.,Agriotes spp., Anthonomus spp., Apion spp., Apogonia spp., Aulacophoraspp., Bruchus spp., Cerosterna spp., Cerotoma spp., Ceutorhynchus spp.,Chaetocnema spp., Colaspis spp., Ctenicera spp., Curculio spp.,Cyclocephala spp., Diabrotica spp., Hypera spp., Ips spp., Lyctus spp.,Megascelis spp., Meligethes spp., Otiorhynchus spp., Pantomorus spp.,Phyllophaga spp., Phyllotreta spp., Rhizotrogus spp., Rhynchites spp.,Rhynchophorus spp., Scolytus spp., Sphenophorus spp., Sitophilus spp.,and Tribolium spp. A non-exhaustive list of particular species includes,but is not limited to, Acanthoscelides obtectus, Agrilus planipennis,Anoplophora glabripennis, Anthonomus grandis, Ataenius spretulus,Atomaria linearis, Bothynoderes punctiventris, Bruchus pisorum,Callosobruchus maculatus, Carpophilus hemipterus, Cassida vittata,Cerotoma trifurcata, Ceutorhynchus assimilis, Ceutorhynchus napi,Conoderus scalaris, Conoderus stigmosus, Conotrachelus nenuphar, Cotinisnitida, Crioceris asparagi, Cryptolestes ferrugineus, Cryptolestespusillus, Cryptolestes turcicus, Cylindrocopturus adspersus, Deporausmarginatus, Dermestes lardarius, Dermestes maculatus, Epilachnavarivestis, Faustinus cubae, Hylobius pales, Hypera postica,Hypothenemus hampei, Lasioderma serricorne, Leptinotarsa decemlineata,Liogenys fuscus, Liogenys suturalis, Lissorhoptrus oryzophilus,Maecolaspis joliveti, Melanotus communis, Meligethes aeneus, Melolonthamelolontha, Oberea brevis, Oberea linearis, Oryctes rhinoceros,Oryzaephilus mercator, Oryzaephilus surinamensis, Oulema melanopus,Oulema oryzae, Phyllophaga cuyabana, Popillia japonica, Prostephanustruncatus, Rhyzopertha dominica, Sitona lineatus, Sitophilus granarius,Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum, Triboliumcastaneum, Tribolium confusum, Trogoderma variabile, and Zabrustenebrioides.

In another embodiment, the compounds according to formula (I) may beused to control pests of the Order Dermaptera.

In another embodiment, the compounds according to formula (I) may beused to control pests of the Order Blattaria. A non-exhaustive list ofparticular species includes, but is not limited to, Blattella germanica,Blatta orientalis, Parcoblatta pennsylvanica, Periplaneta americana,Periplaneta australasiae, Periplaneta brunnea, Periplaneta fuliginosa,Pycnoscelus surinamensis, and Supella longipalpa.

In another embodiment, the compounds according to formula (I) may beused to control pests of the Order Diptera. A non-exhaustive list ofparticular genera includes, but is not limited to, Aedes spp., Agromyzaspp., Anastrepha spp., Anopheles spp., Bactrocera spp., Ceratitis spp.,Chrysops spp., Cochliomyia spp., Contarinia spp., Culex spp., Dasineuraspp., Delia spp., Drosophila spp., Fannia spp., Hylemyia spp., Liriomyzaspp., Musca spp., Phorbia spp., Tabanus spp., and Tipula spp. Anon-exhaustive list of particular species includes, but is not limitedto, Agromyza frontella, Anastrepha suspensa, Anastrepha ludens,Anastrepha obliqa, Bactrocera cucurbitae, Bactrocera dorsalis,Bactrocera invadens, Bactrocera zonata, Ceratitis capitata, Dasineurabrassicae, Delia platura, Fannia canicularis, Fannia scalaris,Gasterophilus intestinalis, Gracillia perseae, Haematobia irritans,Hypoderma lineatum, Liriomyza brassicae, Melophagus ovinus, Muscaautumnalis, Musca domestica, Oestrus ovis, Oscinella fit, Pegomya betae,Psila rosae, Rhagoletis cerasi, Rhagoletis pomonella, Rhagoletis mendax,Sitodiplosis mosellana, and Stomoxys calcitrans.

In another embodiment, the compounds according to formula (I) may beused to control pests of the Order Hemiptera. A non-exhaustive list ofparticular genera includes, but is not limited to, Adelges spp.,Aulacaspis spp., Aphrophora spp., Aphis spp., Bemisia spp., Ceroplastesspp., Chionaspis spp., Chrysomphalus spp., Coccus spp., Empoasca spp.,Lepidosaphes spp., Lagynotomus spp., Lygus spp., Macrosiphum spp.,Nephotettix spp., Nezara spp., Phiiaenus spp., Phytocoris spp.,Piezodorus spp., Planococcus spp., Pseudococcus spp., Rhopalosiphumspp., Saissetia spp., Therioaphis spp., Toumeyella spp., Toxoptera spp.,Trialeurodes spp., Triatoma spp. and Unaspis spp. A non-exhaustive listof particular species includes, but is not limited to, Acrosternumhilare, Acyrthosiphon pisum, Aleyrodes proletella, Aleurodicusdispersus, Aleurothrixus floccosus, Amrasca biguttula biguttula,Aonidiella aurantii, Aphis gossypii, Aphis glycines, Aphis pomi,Aulacorthum solani, Bemisia argentifolii, Bemisia tabaci, Blissusleucopterus, Brachycorynella asparagi, Brevennia rehi, Brevicorynebrassicae, Calocoris norvegicus, Ceroplastes rubens, Cimex hemipterus,Cimex lectularius, Dagbertus fasciatus, Dichelops furcatus, Diuraphisnoxia, Diaphorina citri, Dysaphis plantaginea, Dysdercus suturellus,Edessa meditabunda, Eriosoma lanigerum, Eurygaster maura, Euschistusheros, Euschistus servus, Helopeltis antonii, Helopeltis theivora,Icerya purchasi, Idioscopus nitidulus, Laodelphax striatellus,Leptocorisa oratorius, Leptocorisa varicornis, Lygus hesperus,Maconellicoccus hirsutus, Macrosiphum euphorbiae, Macrosiphum granarium,Macrosiphum rosae, Macrosteles quadrilineatus, Mahanarva frimbiolata,Metopolophium dirhodum, Mictis longicornis, Myzus persicae, Nephotettixcinctipes, Neurocolpus longirostris, Nezara viridula, Nilaparvatalugens, Parlatoria pergandii, Parlatoria ziziphi, Peregrinus maidis,Phylloxera vitifoliae, Physokermes piceae, Phytocoris californicus,Phytocoris relativus, Piezodorus guildinii, Poecilocapsus lineatus,Psallus vaccinicola, Pseudacysta perseae, Pseudococcus brevipes,Quadraspidiotus perniciosus, Rhopalosiphum maidis, Rhopalosiphum padi,Saissetia oleae, Scaptocoris castanea, Schizaphis graminum, Sitobionavenae, Sogatella furcifera, Trialeurodes vaporariorum, Trialeurodesabutiloneus, Unaspis yanonensis, and Zulia entrerriana.

In another embodiment, the compounds according to formula (I) may beused to control pests of the Order Hymenoptera. A non-exhaustive list ofparticular genera includes, but is not limited to, Acromyrmex spp., Attaspp., Camponotus spp., Diprion spp., Formica spp., Monomorium spp.,Neodiprion spp., Pogonomyrmex spp., Polistes spp., Solenopsis spp.,Vespula spp., and Xylocopa spp. A non-exhaustive list of particularspecies includes, but is not limited to, Athalia rosae, Atta texana,Iridomyrmex humilis, Monomorium minimum, Monomorium pharaonis,Solenopsis invicta, Solenopsis geminata, Solenopsis molesta, Solenopsisrichtery, Solenopsis xyloni, and Tapinoma sessile.

In another embodiment, the compounds according to formula (I) may beused to control pests of the Order Isoptera. A non-exhaustive list ofparticular genera includes, but is not limited to, Coptotermes spp.,Cornitermes spp., Cryptotermes spp., Heterotermes spp., Kalotermes spp.,Incisitermes spp., Macrotermes spp., Marginitermes spp., Microcerotermesspp., Procornitermes spp., Reticulitermes spp., Schedorhinotermes spp.,and Zootermopsis spp. A non-exhaustive list of particular speciesincludes, but is not limited to, Coptotermes curvignathus, Coptotermesfrenchi, Coptotermes formosanus, Heterotermes aureus, Microtermes obesi,Reticulitermes banyulensis, Reticulitermes grassei, Reticulitermesflavipes, Reticulitermes hageni, Reticulitermes hesperus, Reticulitermessantonensis, Reticulitermes speratus, Reticulitermes tibialis, andReticulitermes virginicus.

In another embodiment, the compounds according to formula (I) may beused to control pests of the Order Lepidoptera. A non-exhaustive list ofparticular genera includes, but is not limited to, Adoxophyes spp.,Agrotis spp., Argyrotaenia spp., Cacoecia spp., Caloptilia spp., Chilospp., Chrysodeixis spp., Colias spp., Crambus spp., Diaphania spp.,Diatraea spp., Earias spp., Ephestia spp., Epimecis spp., Feltia spp.,Gortyna spp., Helicoverpa spp., Heliothis spp., Indarbela spp.,Lithocolletis spp., Loxagrotis spp., Malacosoma spp., Peridroma spp.,Phyllonorycter spp., Pseudaletia spp., Sesamia spp., Spodoptera spp.,Synanthedon spp., and Yponomeuta spp. A non-exhaustive list ofparticular species includes, but is not limited to, Achaea janata,Adoxophyes orana, Agrotis ipsilon, Alabama argillacea, Amorbia cuneana,Amyelois transitella, Anacamptodes defectaria, Anarsia lineatella,Anomis sabulifera, Anticarsia gemmatalis, Archips argyrospila, Archipsrosana, Argyrotaenia citrana, Autographa gamma, Bonagota cranaodes,Borbo cinnara, Bucculatrix thurberiella, Capua reticulana, Carposinaniponensis, Chlumetia transversa, Choristoneura rosaceana,Cnaphalocrocis medinalis, Conopomorpha cramerella, Cossus cossus, Cydiacaryana, Cydia funebrana, Cydia molesta, Cydia nigricans, Cydiapomonella, Darna diducta, Diatraea saccharalis, Diatraea grandiosella,Earias insulana, Earias vittella, Ecdytolopha aurantianum, Elasmopalpuslignosellus, Ephestia cautella, Ephestia elutella, Ephestia kuehniella,Epinotia aporema, Epiphyas postvittana, Erionota thrax, Eupoeciliaambiguella, Euxoa auxiliaris, Grapholita molesta, Hedylepta indicata,Helicoverpa armigera, Helicoverpa zea, Heliothis virescens, Hellulaundalis, Keiferia lycopersicella, Leucinodes orbonalis, Leucopteracoffeella, Leucoptera malifoliella, Lobesia botrana, Loxagrotisalbicosta, Lymantria dispar, Lyonetia clerkella, Mahasena corbetti,Mamestra brassicae, Maruca testulalis, Metisa plana, Mythimna unipuncta,Neoleucinodes elegantalis, Nymphula depunctalis, Operophtera brumata,Ostrinia nubilalis, Oxydia vesulia, Pandemis cerasana, Pandemisheparana, Papilio demodocus, Pectinophora gossypiella, Peridroma saucia,Perileucoptera coffeella, Phthorimaea operculella, Phyllocnistiscitrella, Pieris rapae, Plathypena scabs, Plodia interpunctella,Plutella xylostella, Polychrosis viteana, Prays endocarps, Prays oleae,Pseudaletia unipuncta, Pseudoplusia includens, Rachiplusia nu,Scirpophaga incertulas, Sesamia inferens, Sesamia nonagrioides, Setoranitens, Sitotroga cerealella, Sparganothis pilleriana, Spodopteraexigua, Spodoptera frugiperda, Spodoptera eridania, Thecla basilides,Tineola bisselliella, Trichoplusia ni, Tuta absoluta, Zeuzera coffeae,and Zeuzera pyrina.

In another embodiment, the compounds according to formula (I) may beused to control pests of the Order Mallophaga. A non-exhaustive list ofparticular genera includes, but is not limited to, Anaticola spp.,Bovicola spp., Chelopistes spp., Goniodes spp., Menacanthus spp., andTrichodectes spp. A non-exhaustive list of particular species includes,but is not limited to, Bovicola bovis, Bovicola caprae, Bovicola ovis,Chelopistes meleagridis, Goniodes dissimilis, Goniodes gigas,Menacanthus stramineus, Menopon gallinae, and Trichodectes canis.

In another embodiment, the compounds according to formula (I) may beused to control pests of the Order Orthoptera. A non-exhaustive list ofparticular genera includes, but is not limited to, Melanoplus spp., andPterophylla spp. A non-exhaustive list of particular species includes,but is not limited to, Anabrus simplex, Gryllotalpa africana,Gryllotalpa australis, Gryllotalpa brachyptera, Gryllotalpa hexadactyla,Locusta migratoria, Microcentrum retinerve, Schistocerca gregaria, andScudderia furcata.

In another embodiment, the compounds according to formula (I) may beused to control pests of the Order Siphonaptera. A non-exhaustive listof particular species includes, but is not limited to, Ceratophyllusgallinae, Ceratophyllus niger, Ctenocephalides canis, Ctenocephalidesfelis, and Pulex irritans.

In another embodiment, the compounds according to formula (I) may beused to control pests of the Order Thysanoptera. A non-exhaustive listof particular genera includes, but is not limited to, Caliothrips spp.,Frankliniella spp., Scirtothrips spp., and Thrips spp. A non-exhaustivelist of particular sp. includes, but is not limited to, Frankliniellafusca, Frankliniella occidentalis, Frankliniella schultzei,Frankliniella williamsi, Heliothrips haemorrhoidalis, Rhipiphorothripscruentatus, Scirtothrips citri, Scirtothrips dorsalis, and Taeniothripsrhopalantennalis, Thrips hawaiiensis, Thrips nigropilosus, Thripsorientalis, Thrips tabaci.

In another embodiment, the compounds according to formula (I) may beused to control pests of the Order Thysanura. A non-exhaustive list ofparticular genera includes, but is not limited to, Lepisma spp. andThermobia spp.

In another embodiment, the compounds according to formula (I) may beused to control pests of the Order Acarina. A non-exhaustive list ofparticular genera includes, but is not limited to, Acarus spp., Aculopsspp., Boophilus spp., Demodex spp., Dermacentor spp., Epitrimerus spp.,Eriophyes spp., Ixodes spp., Oligonychus spp., Panonychus spp.,Rhizoglyphus spp., and Tetranychus spp. A non-exhaustive list ofparticular species includes, but is not limited to, Acarapis woodi,Acarus siro, Aceria mangiferae, Aculops lycopersici, Aculus pelekassi,Aculus schlechtendali, Amblyomma americanum, Brevipalpus obovatus,Brevipalpus phoenicis, Dermacentor variabilis, Dermatophagoidespteronyssinus, Eotetranychus carpini, Notoedres cati, Oligonychuscoffeae, Oligonychus ilicis, Panonychus citri, Panonychus ulmi,Phyllocoptruta oleivora, Polyp hagotarsonemus latus, Rhipicephalussanguineus, Sarcoptes scabiei, Tegolophus perseaflorae, Tetranychusurticae, and Varroa destructor.

In another embodiment, the compounds according to formula (I) may beused to control pest of the Order Symphyla. A non-exhaustive list ofparticular sp. includes, but is not limited to, Scutigerella immaculata.

In another embodiment, the compounds according to formula (I) may beused to control pests of the Phylum Nematoda. A non-exhaustive list ofparticular genera includes, but is not limited to, Aphelenchoides spp.,Belonolaimus spp., Criconemella spp., Ditylenchus spp., Heterodera spp.,Hirschmanniella spp., Hoplolaimus spp., Meloidogyne spp., Pratylenchusspp., and Radopholus spp. A non-exhaustive list of particular sp.includes, but is not limited to, Dirofilaria immitis, Heterodera zeae,Meloidogyne incognita, Meloidogyne javanica, Onchocerca volvulus,Radopholus similis, and Rotylenchulus reniformis.

For additional information consult “HANDBOOK OF PEST CONTROL—THEBEHAVIOR, LIFE HISTORY, AND CONTROL OF HOUSEHOLD PEST” by Arnold Mallis,9th Edition, copyright 2004 by GIE Media Inc.

Applications

Compounds according to formula (I) are generally used in amounts fromabout 0.01 grams per hectare to about 5000 grams per hectare to providecontrol. Amounts from about 0.1 grams per hectare to about 500 grams perhectare are generally preferred, and amounts from about 1 gram perhectare to about 50 grams per hectare are generally more preferred.

The area to which a compound according to formula (I) is applied can beany area inhabited (or maybe inhabited, or traversed by) a pest, forexample: where crops, trees, fruits, cereals, fodder species, vines,turf and ornamental plants, are growing; where domesticated animals areresiding; the interior or exterior surfaces of buildings (such as placeswhere grains are stored), the materials of construction used in building(such as impregnated wood), and the soil around buildings. Particularcrop areas to use a compound according to formula (I) include areaswhere apples, corn, sunflowers, cotton, soybeans, canola, wheat, rice,sorghum, barley, oats, potatoes, oranges, alfalfa, lettuce,strawberries, tomatoes, peppers, crucifers, pears, tobacco, almonds,sugar beets, beans and other valuable crops are growing or the seedsthereof are going to be planted. It is also advantageous to use ammoniumsulfate with a molecule of Formula One when growing various plants.

Controlling pests generally means that pest populations, pest activity,or both, are reduced in an area. This can come about when: pestpopulations are repulsed from an area; when pests are incapacitated inor around an area; or pests are exterminated, in whole, or in part, inor around an area. Of course, a combination of these results can occur.Generally, pest populations, activity, or both are desirably reducedmore than fifty percent, preferably more than 90 percent. Generally, thearea is not in or on a human; consequently, the locus is generally anon-human area.

The compounds according to formula (I) may be used in mixtures, appliedsimultaneously or sequentially, alone or with other compounds to enhanceplant vigor (e.g. to grow a better root system, to better withstandstressful growing conditions). Such other compounds are, for example,compounds that modulate plant ethylene receptors, most notably1-methylcyclopropene (also known as 1-MCP). Furthermore, such compoundsmay be used during times when pest activity is low, such as before theplants that are growing begin to produce valuable agriculturalcommodities. Such times include the early planting season when pestpressure is usually low.

The compounds according to formula (I) can be applied to the foliar andfruiting portions of plants to control pests. The compounds will eithercome in direct contact with the pest, or the pest will consume thepesticide when eating leaf, fruit mass, or extracting sap, that containsthe pesticide. The compounds according to formula (I) can also beapplied to the soil, and when applied in this manner, root and stemfeeding pests can be controlled. The roots can absorb a compound takingit up into the foliar portions of the plant to control above groundchewing and sap feeding pests.

Generally, with baits, the baits are placed in the ground where, forexample, termites can come into contact with, and/or be attracted to,the bait. Baits can also be applied to a surface of a building,(horizontal, vertical, or slant surface) where, for example, ants,termites, cockroaches, and flies, can come into contact with, and/or beattracted to, the bait. Baits can comprise a compound according toformula (I).

The compounds according to formula (I) can be encapsulated inside, orplaced on the surface of a capsule. The size of the capsules can rangefrom nanometer size (about 100-900 nanometers in diameter) to micrometersize (about 10-900 microns in diameter).

Because of the unique ability of the eggs of some pests to resistcertain pesticides, repeated applications of the compounds according toformula (I) may be desirable to control newly emerged larvae.

Systemic movement of pesticides in plants may be utilized to controlpests on one portion of the plant by applying (for example by sprayingan area) the compounds according to formula (I) to a different portionof the plant. For example, control of foliar-feeding insects can beachieved by drip irrigation or furrow application, by treating the soilwith for example pre- or post-planting soil drench, or by treating theseeds of a plant before planting.

Seed treatment can be applied to all types of seeds, including thosefrom which plants genetically modified to express specialized traitswill germinate. Representative examples include those expressingproteins toxic to invertebrate pests, such as Bacillus thuringiensis orother insecticidal toxins, those expressing herbicide resistance, suchas “Roundup Ready” seed, or those with “stacked” foreign genesexpressing insecticidal toxins, herbicide resistance,nutrition-enhancement, drought resistance, or any other beneficialtraits. Furthermore, such seed treatments with the compounds accordingto formula (I) may further enhance the ability of a plant to betterwithstand stressful growing conditions. This results in a healthier,more vigorous plant, which can lead to higher yields at harvest time.Generally, about 1 gram of the compounds according to formula (I) toabout 500 grams per 100,000 seeds is expected to provide good benefits,amounts from about 10 grams to about 100 grams per 100,000 seeds isexpected to provide better benefits, and amounts from about 25 grams toabout 75 grams per 100,000 seeds is expected to provide even betterbenefits.

It should be readily apparent that the compounds according to formula(I) may be used on, in, or around plants genetically modified to expressspecialized traits, such as Bacillus thuringiensis or other insecticidaltoxins, or those expressing herbicide resistance, or those with“stacked” foreign genes expressing insecticidal toxins, herbicideresistance, nutrition-enhancement, or any other beneficial traits.

The compounds according to formula (I) may be used for controllingendoparasites and ectoparasites in the veterinary medicine sector or inthe field of non-human animal keeping. The compounds according toformula (I) are applied, such as by oral administration in the form of,for example, tablets, capsules, drinks, granules, by dermal applicationin the form of, for example, dipping, spraying, pouring on, spotting on,and dusting, and by parenteral administration in the form of, forexample, an injection.

The compounds according to formula (I) may also be employedadvantageously in livestock keeping, for example, cattle, sheep, pigs,chickens, and geese. They may also be employed advantageously in petssuch as, horses, dogs, and cats. Particular pests to control would befleas and ticks that are bothersome to such animals. Suitableformulations are administered orally to the animals with the drinkingwater or feed. The dosages and formulations that are suitable depend onthe species.

The compounds according to formula (I) may also be used for controllingparasitic worms, especially of the intestine, in the animals listedabove.

The compounds according to formula (I) may also be employed intherapeutic methods for human health care. Such methods include, but arelimited to, oral administration in the form of, for example, tablets,capsules, drinks, granules, and by dermal application.

Pests around the world have been migrating to new environments (for suchpest) and thereafter becoming a new invasive species in such newenvironment. The compounds according to formula (I) may also be used onsuch new invasive species to control them in such new environment.

The compounds according to formula (I) may also be used in an area whereplants, such as crops, are growing (e.g. pre-planting, planting,pre-harvesting) and where there are low levels (even no actual presence)of pests that can commercially damage such plants. The use of suchcompounds in such area is to benefit the plants being grown in the area.Such benefits, may include, but are not limited to, improving the healthof a plant, improving the yield of a plant (e.g. increased biomassand/or increased content of valuable ingredients), improving the vigorof a plant (e.g. improved plant growth and/or greener leaves), improvingthe quality of a plant (e.g. improved content or composition of certainingredients), and improving the tolerance to abiotic and/or bioticstress of the plant.

Before a pesticide can be used or sold commercially, such pesticideundergoes lengthy evaluation processes by various governmentalauthorities (local, regional, state, national, and international).Voluminous data requirements are specified by regulatory authorities andmust be addressed through data generation and submission by the productregistrant or by a third party on the product registrant's behalf, oftenusing a computer with a connection to the World Wide Web. Thesegovernmental authorities then review such data and if a determination ofsafety is concluded, provide the potential user or seller with productregistration approval. Thereafter, in that locality where the productregistration is granted and supported, such user or seller may use orsell such pesticide.

A compound according to formula (I) can be tested to determine itsefficacy against pests. Furthermore, mode of action studies can beconducted to determine if said compound has a different mode of actionthan other pesticides. Thereafter, such acquired data can bedisseminated, such as by the internet, to third parties.

The compounds according to formula (I) will generally have a molecularmass of about 100 Daltons to about 1200 Daltons. However, it isgenerally preferred if the molecular mass is from about 120 Daltons toabout 900 Daltons, and it is even more generally preferred if themolecular mass is from about 140 Daltons to about 600 Daltons.

EXAMPLES

The examples are for illustration purposes and are not to be construedas limiting the invention disclosed in this document to only theembodiments disclosed in these examples.

Starting materials, reagents, and solvents that were obtained fromcommercial sources were used without further purification Anhydroussolvents were purchased as Sure/Seal™ from Aldrich and were used asreceived. Melting points were obtained on a Thomas Hoover Unimeltcapillary melting point apparatus or an OptiMelt Automated Melting PointSystem from Stanford Research Systems and are uncorrected. Molecules aregiven their known names, named according to naming programs within ISISDraw, ChemDraw or ACD Name Pro. If such programs are unable to name amolecule, the molecule is named using conventional naming rules. ¹H NMRspectral data are in ppm (δ) and were recorded at 300, 400 or 600 MHz,and ¹³C NMR spectral data are in ppm (δ) and were recorded at 75, 100 or150 MHz, unless otherwise stated.

Compounds according to formula (I) can be prepared by the methodsillustrated in Schemes I-IV below.

In Scheme I, compounds according to formula (III), where R⁴, R⁵ and R⁶are as previously defined, can be prepared as in step a, from compoundsaccording to formula (II) through a Curtius rearrangement, usingreagents such as diphenylphosphoryl azide in a solvent such as tolueneand a base such as triethylamine in the presence of tert-butanol.Compounds according to formula (II) where R⁴, R⁵, and R⁶ are aspreviously defined are available from a variety of different commercialsources. Compounds of formula (IV), where R³ does not represent H but isotherwise as previously defined and each of R⁴, R⁵ and R⁶ is aspreviously defined, can be prepared as in step b, from a compoundaccording to formula (III) using a base such as sodium hydride in asolvent such as DMF and an alkylating reagent such as methyl iodide.

In Scheme II above, compounds according to formula (V) can be preparedfrom compounds according to formula (IV), where R³ does not represent Hbut is otherwise as previously defined and each of R⁴, R⁵, and R⁶ is aspreviously defined, as in step a using standard deprotecting conditionssuch as trifluoroacetic acid in methylene chloride. Compounds accordingto formula (Ia), where R² represents H, R³ does not represent H but isotherwise as previously defined and each of R¹, R⁴, R⁵ and R⁶ is aspreviously defined, can be prepared as in step b by combining compoundsaccording to formula (V) with compounds according to formula (VI), whereR¹ is as previously defined and R⁷ represents F, in a solvent such asTHF or methylene chloride. Compounds according to formula (VI), such as2-isocyanato-4,6-bis(trifluoroethoxy)pyrimidine and5-fluoro-2-isocyanato-4,6-bis(trifluoroethoxy)pyrimidine, can beprepared as disclosed in U.S. Pat. No. 8,013,154(B2), the contents ofwhich are incorporated herein by reference in their entirety.

In Scheme III above, compounds according to formula (VII) can beprepared from compounds according to formula (III), where each of R⁴,R⁵, and R⁶ is as previously defined, as in step a using standarddeprotecting conditions such as trifluoroacetic acid in methylenechloride. Compounds according to formula (Ib), where each of R² and R³represents H and each of R¹, R⁴, R⁵ and R⁶ is as previously defined, canbe prepared as in step b by combining compounds according to formula(VII) with compounds according to formula (VI), where R¹ is aspreviously defined, in a solvent such as THF or methylene chloride.

In Scheme IV above, compounds according to Formula (Ic), where R² and R³do not represent H but are as otherwise previously defined and each ofR¹, R⁴, R⁵ and R⁶ is as previously defined, can be prepared fromcompounds according to Formula (Ia), where R² represents H, R³ does notrepresent H but is as otherwise previously defined and each of R¹, R⁴,R⁵ and R⁶ is as previously defined, as in step a, using a base such assodium hydride in a solvent such as THF, followed by reaction with anelectrophilic reagent such as benzyloxymethyl chloride or other alkylelectrophile.

In Scheme V above, compounds according to formula (Id), where R² doesnot represent H but is otherwise as previously defined, R³ represents H,and each of R¹, R⁴, R⁵ and R⁶ is as previously defined, can be preparedfrom compounds according to formula (Ib), where R² and R³ represent Hand each of R¹, R⁴, R⁵ and R⁶ is as previously defined, as in step a,using a base such as sodium hydride in a solvent such as THF, followedby reaction with an electrophilic reagent such as benzyloxymethylchloride or other alkyl electrophile. Compounds according to formula(Ic), where R² and R³ do not represent H but are otherwise as previouslydefined and each of R¹, R⁴, R⁵ and R⁶ is as previously defined, can beprepared from compounds according to formula (Id) as in step b, using abase such as sodium hydride and a solvent such as THF, followed byreaction with an electrophilic reagent such as methyl iodide or otheralkyl electrophile. Steps a and b can also be performed in one processwhereby a compound according to formula (Ib) is treated with two or moreequivalents of a base, such as sodium hydride, and then is treated withtwo or more equivalents of an electrophile, such as methyl iodide.

In Scheme VI above, compounds according to formula (Ic) where R² and R³do not represent H but are otherwise as previously defined and each ofR¹, R⁴, R⁵ and R⁶ is as previously defined, can be prepared fromcompounds according to formula (Id) where R² does not represent H but isotherwise as previously defined, R³ represents H, and each of R¹, R⁴, R⁵and R⁶ is as previously defined, as in step a, using a base such assodium hydride and a solvent such as THF, followed by reaction with anelectrophilic reagent such as methoxy or other alkyl electrophile.

In Scheme VII above, compounds according to formula (Ia) where R²represents H, R³ does not represent H but is otherwise as previouslydefined and each of R¹, R⁴, R⁵ and R⁶ is as previously defined, can beprepared from compounds according to formula (Ic) where R² and R³ do notrepresent H but are as otherwise previously defined and each of R¹, R⁴,R⁵ and R⁶ is as previously defined, as in step a, by removal of R² whenR² is such a group that can be removed without removal of R³ (forexample see: Protecting Groups in Organic Synthesis, Third Edition, T.W. Greene and P. G. M. Wuts, John Wiley and Sons, Inc., 1999).

Example 1 Preparation of tert-butyl5-(trifluoromethyl)thiophen-2-ylcarbamate

To 5-(trifluoromethyl)thiophene-2-carboxylic acid in tBuOH (50 mL) wasadded triethylamine (1.53 mL, 11 mmol) and diphenylphosphoryl azide(DPPA) (2.4 mL, 11 mmol). This mixture was heated to 90° C., and wasstirred overnight (ca. 16 hours). Thin layer chromatography (TLC)indicated that the reaction was complete. The solvent was removed underreduced pressure, the residue was dissolved in ethyl acetate (EtOAc) andwashed 1× with NaHCO₃ aq sat, 1× with citric acid (10% aqueous), and 1×brine. The solution was dried over MgSO₄, filtered and concentrated.After silica gel chromatography (5 to 20% EtOAc/hexanes) the titlecompound was afforded (1.46 g, 44% over 3 steps) as a yellow/orangesolid, mp 118-120° C.; R_(f)=0.31 (10% EtOAc/hex); ¹H NMR (DMSO-d₆) δ11.03 (br s, 1H), 7.38 (app d, 1H, J=4.1 Hz), 6.51 (app d, 1H, J=3.3Hz), 1.49 (s, 9H); GCMS (EI) m/z 267 (M⁺).

Example 2 Preparation of N-Methyl-5-(trifluoromethyl)thiophen-2-amine

To tert-butyl 5-(trifluoromethyl)thiophen-2-ylcarbamate (0.40 g, 1.5mmol) in DMF (9 mL) at 0° C. was added NaH (72 mg, 1.8 mmol, 60%dispersion in mineral oil) in one portion. After 40 minutes MeI (0.20mL, 1.8 mmol) was added via syringe. After stirring for 30 minutes at 0°C., TLC of a quenched aliquot showed the reaction was complete. Thereaction was quenched by pouring into a biphasic mixture of 1N HCl andEtOAc. The layers were separated, and the organic layer was washed 3×with H₂O, 1× with brine, dried over MgSO₄, filtered, and concentratedunder reduced pressure to afford a yellow oil. The crude oil was addedto CH₂Cl₂ (2 mL) and trifluoroacetic acid (2 mL). After this mixture hadbeen stirred at ambient temperature for 80 minutes, TLC showed thereaction was complete. The solvents were removed under reduced pressureand the residue was taken up in CH₂Cl₂ and was washed with NaHCO₃ aqsat. This aqueous wash was back extracted 1× with CH₂Cl₂, then thecombined organic layers were dried over MgSO₄, filtered, andconcentrated under reduced pressure.N-Methyl-5-(trifluoromethyl)thiophen-2-amine was used directly in thenext step.

Example 3 Preparation of 5-methylthiophen-2-amine hydrochloride

To a solution of an N-Boc protected 5-methylthiophen-2-amine compound(0.5 g, 2.35 mmol) in 1,4-dioxane (5 mL) was added HCl in 1,4-dioxane (5mL) at 0° C. and the mixture was stirred at room temperature for 16hours. The solvent was evaporated under reduced pressure and the residueobtained was washed with Et₂O to give the title compound (25 g, 71.4%).

Example 4 Preparation of3-(4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl)-1-methyl-1-(5-(trifluoromethyl)thiophen-2-yl)urea(2)

To a solution of N-methyl-5-(trifluoromethyl)thiophen-2-amine in CH₂Cl₂(2 mL) was added 2-isocyanato-4,6-bis(2,2,2-trifluoroethoxy)pyrimidine(1.6 mL, 1.0 M in THF) (prepared as described in U.S. Pat. No.8,013,154, the contents of which were incorporated herein above byreference in their entirety). This reaction was stirred at ambienttemperature overnight. TLC indicated the reaction was complete. Thesolvent was removed under reduced pressure and the residue was purifiedusing normal phase chromatography which afforded product (471 mg, 56%over three steps) as an off-white solid, mp 99-101° C.: R_(f)=0.26 (30%EtOAc, hex); ¹H NMR (DMSO-d₆) 10.34 (s, 1H), 7.48 (d, 1H, J=3.3 Hz),6.78 (d, 1H, J=4.3 Hz), 6.28 (s, 1H), 5.02 (q, 4H, J=17.8, 8.9 Hz), 3.49(s, 3H); ESIMS m/z 497 [(M-1)+].

Example 5 Preparation of3-methyl-3-(4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl)-1-methyl-1-(5-(trifluoromethyl)thiophen-2-yl)urea(6)

To a suspension of NaH (18 mg, 0.36 mmol) in anhydrous THF (3 mL) wasadded a solution of the3-(4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl)-1-methyl-1-(5-(trifluoromethyl)thiophen-2-yl)urea(2) (150 mg, 0.30 mmol). The reaction was stirred for 10 minutes afterwhich time gas evolution had subsided. To the reaction was added methyliodide (51.2 mg, 0.36 mmol). The reaction was stirred at ambienttemperature for 2 h. The reaction was quenched with H₂O (5 mL) andextracted with t-butyl ethyl ether (3×5 mL). The organics were combinedand extracted with an equal amount of H₂O. The organics were dried(MgSO₄), filtered and concentrated to afford crude product. The crudematerial was purified by silica gel chromatography (5% EtOAc in petether) to afford3-methyl-3-(4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl)-1-methyl-1-(5-(trifluoromethyl)thiophen-2-yl)urea(6) as an off white solid (31 mg, 20%), mp 113-114° C.; ¹H NMR (400 MHz,Acetone-d₆) δ 7.35-7.24 (m, 1H), 6.73 (d, J=4.2 Hz, 1H), 5.88 (s, 1H),4.76 (q, J=8.7 Hz, 4H), 3.35 (s, 3H), 3.28 (s, 3H); ESIMS m/z 513([M+H]+).

Example 6 Preparation of3-(methoxymethyl)-3-(4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl)-1-(5-(trifluoromethyl)thiophen-2-yl)urea(4)

To a solution of3-(4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl)-1-(5-(trifluoromethyl)thiophen-2-yl)urea(1) (150 mg, 0.31 mmol) in anhydrous dimethyl formamide (DMF, 1.5 mL) atambient temperature was added NaH (6.6 mg, 0.28 mmol, 60% dispersion inmineral oil). After stirring 20 minutes a solution of bromomethyl methylether (35 mg, 0.28 mmol) in anhydrous DMF (0.5 mL) was added. After 2.5h the reaction was judged complete by TLC analysis. To the reaction wascarefully added H₂O (2 mL). The reaction was extracted with EtOAc (10mL). The EtOAc solution was washed with H₂O (3×7 mL) followed by brine(7 mL). The organics were dried (Na₂SO₄), filtered and evaporated togive crude product. The crude material was purified by silica gelchromatography (0 to 8% EtOAc in pet ether) to afford3-(methoxymethyl)-3-(4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl)-1-(5-(trifluoromethyl)thiophen-2-yl)urea(4) as an off white solid (18 mg, 11%), mp 118-119° C.; ¹H NMR (400 MHz,Acetone-d₆) δ 11.84 (s, 1H), 7.41-7.28 (m, 1H), 6.66 (dd, J=4.1, 0.9 Hz,1H), 6.18 (s, 1H), 5.54 (s, 2H), 5.02 (q, J=8.6 Hz, 4H), 3.27 (s, 3H);ESIMS m/z 527 ([M−H]+).

Example 7 Preparation of3-(benzyloxymethyl)-3-(4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl)-1-(methoxymethyl)-1-(5-(trifluoromethyl)thiophen-2-yl)urea(10)

To a solution of3-(benzyloxymethyl)-3-(4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl)-1-(5-(trifluoromethyl)thiophen-2-yl)urea(250 mg, 0.41 mmol) in anhydrous DMF (2.5 mL), with an internaltemperature of ≦−10° C., was slowly added NaH (20 mg, 0.5 mmol, 60%dispersion in mineral oil). The mixture was stirred 30 minutes resultingin a clear yellow solution. To this solution was slowly added a solutionof bromomethyl methyl ether (51.6 mg, 0.41 mmol) in anhydrous DMF (0.5mL). After 2.5 h the reaction was quenched with ice and diluted withEtOAc (25 mL). The mixture was extracted with H₂O (3×15 mL) and brine(15 mL). The EtOAc solution was dried (Na₂SO₄), filtered and evaporatedto give crude product. The crude product was purified by silica gelchromatography (2 to 6% EtOAc in pet ether) to afford the product as apale yellow gum (185 mg, 69%). ¹H NMR (400 MHz, Acetone-d₆) δ 7.29-7.08(m, 6H), 6.82 (d, J=3.9 Hz, 1H), 5.90 (s, 1H), 5.40 (s, 2H), 5.10 (s,2H), 4.79 (q, J=8.7 Hz, 4H), 4.69 (s, 2H), 3.27 (s, 3H); ESIMS m/z 649([M+H]+).

Example 8 Preparation of3-(benzyloxymethyl)-3-(4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl)-1-(5-(trifluoromethyl)thiophen-2-yl)urea

To a solution of3-(4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl)-1-(5-(trifluoromethyl)thiophen-2-yl)urea(1) (750 mg, 1.54 mmol) in anhydrous DMF (7.5 mL) at ambient temperaturewas added NaH (37 mg, 1.54 mmol, 60% dispersion in mineral oil). Afterstirring for 20 minutes a solution of benzyloxymethylchloride (241 mg,1.54 mmol) in anhydrous DMF (0.75 mL) was added. After 2 h of stirringat room temperature the reaction was quenched with H₂O (5 mL) anddiluted with EtOAc. The organic layer was separated and washed with H₂O(3×10 mL) and brine (10 mL). The organics were dried (Na₂SO₄), filteredand evaporated. The crude material was purified by silica gelchromatography (0 to 10% EtOAc in pet ether) to afford3-(benzyloxymethyl)-3-(4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl)-1-(5-(trifluoromethyl)thiophen-2-yl)ureaas an off white solid (550 mg, 59%), mp 101-104° C.; ¹H NMR (400 MHz,Acetone-d₆) δ 11.82 (s, 1H), 7.37-6.99 (m, 5H), 6.65 (d, J=4.0 Hz, 1H),6.17 (s, 1H), 5.71 (s, 2H), 4.97 (q, J=8.5 Hz, 4H), 4.60 (s, 2H); ESIMSm/z 605 ([M+H]+). Also isolated was a by-product1,3-bis(benzyloxymethyl)-3-(4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl)-1-(5-(trifluoromethyl)thiophen-2-yl)urea(11) as a pale yellow gum (65 mg); 1H NMR (400 MHz, Aceton) δ 7.29-7.05(m, 10H), 6.87 (d, J=4.0 Hz, 1H), 5.90 (s, 1H), 5.40 (s, 2H), 5.23 (s,2H), 4.75 (q, J=8.7 Hz, 4H), 4.69 (s, 2H), 4.52 (s, 2H); ESIMS m/z 618([M−PhCH2O]+).

Compounds 1-45 identified in Table 1 were prepared in Examples 4-8,utilizing reactions similar to those described in one or more ofExamples 1-8, and/or in accordance with one or more of Schemes I-VII.Table 1 also identifies precursor or starting compounds used inpreparation of Compounds 1-45. The precursor or starting aminesidentified in connection with Compounds 20-45 were prepared as shown inScheme I (step a or steps a and b) to provide a carbamate which wasdeprotected in accordance with step a of Scheme II or III. Example 3also provides an exemplary deprotection reaction. The Cl analogillustrated in connection with Compounds 20, 29 and 43 resulted fromexchange of Cl for Br during the deprotection reaction. In Compound 21,complete exchange of Cl for Br occurred resulting only in the Clcompound.

TABLE 1 Compound No. Structure Precursor  1

trifluoromethyl thiophen-2- amine  2

N-Methyl-5- (trifluoromethyl) thiophen-2- amine  3

Compound 1, methyl iodide  4

Compound 1, bromomethyl methyl ether  5

Compound 1, chloromethyl acetate  6

Compound 2, methyl iodide  7

Compound 2, bromomethyl methyl ether  8

Compound 2, chloromethyl acetate  9

Compound 2, benzyl bromo methyl ether 10

Refer to Examples 7 and 8 11

Compound 1, benzyl bromo methyl ether 12

5-fluoro-2- isocyanato-4,6- bis(2,2,2- trifluoroethoxy) pyrimidine,trifluoromethyl thiophene- 2amine 13

5-fluoro-2- isocyanato-4,6- bis(2,2,2- trifluoroethoxy) pyrimidine 14

Compound 12, methyl iodide 15

Compound 12, bromomethyl methyl ether 16

Compound 12, benzyl bromo methyl ether 17

Compound 13, methyl iodide 18

Compound 13, bromomethyl methyl ether 19

Compound 13, chloromethyl acetyl 20

  4-bromo-5- ethyl-thiophen- 2-amine

21

4-bromo-5- ethyl-N- methyl- thiophen-2- amine 22

5- chlorothiophen- 2-amine 23

metrhylthiophen- 2-amine 24

5- cyanothiophen- 2-amine 25

4-chloro-3- methoxy- thiophen-2- amine 26

4-(4- chlorophenyl)- N- methylthiophene- 2-amine 27

4- cyanothiophene- 2-amine 28

3-chloro-N- methylthiophene- 2-amine 29

 

3-bromo-N- methylthiophene- 2-amine 30

3,5- dibromothiophene- 2-amine 31

3-methyl-N- methylthiophene- 2-amine 32

3- chlorothiophene- 2-amine 33

3- methoxythiophene- 2-amine 34

4-methyl-N- methylthiophene- 2-amine 35

4-chloro-3- methoxy-N- methylthiophene- 2-amine 36

3-methoxy-N- methylthiophene- 2-amine 37

3- methylthiophene- 2-amine 38

4-cyano-N- methylthiophene- 2-amine 39

5-methyl-N- methylthiophene- 2-amine 40

4-(4- chlorophenyl) thiophene-2- amine 41

5- methylthiophene- 2-amine 42

4-chloro-3- methylthiophene- 2-amine 43

 

4- bromothiophene- 2-amine 44

3,4,5- trichlorothiophene- 2-amine 45

3- bromothiophene- 2-amine

Table 2 provides analytical data associated with Compounds 1-45.

TABLE 2 Appear- MP IR NO. ance (° C.) (cm⁻¹) MASS NMR 1 White 172-174ESIMS m/z 485.3 ¹H NMR (DMSO- Solid ([M + H]⁺), 483.1 d₆) δ 11.27 (s,1H), ([M − H]⁻) 10.70 (s, 1H), 7.52 (dd, J = 4.1, 1.4 Hz, 1H), 6.72 (d,J = 4.1 Hz, 1H), 6.35 (s, 1H), 5.17 (q, J = 17.6, 8.8 Hz, 4H). 2Off-White  99-101 ESIMS m/z 499.3 ¹H NMR (DMSO- Solid ([M + H]⁺), 496.8d₆) δ 10.35 (s, 1H), ([M − H]⁻) 7.49 (d, J = 3.3 Hz, 1H), 6.78 (d, J =4.3 Hz, 1H), 6.29 (s, 1H), 5.00 (q, J = 17.8, 8.9 Hz, 4H), 3.49 (s, 3H).3 Off-white 150.4-151.4 ESIMS m/z 499 ¹H NMR (400 MHz, Solid ([M + H]⁺)Acetone-d₆) δ 12.37 (s, 1H), 7.56-7.26 m, 1H), 6.76 (d, J = 4.1 Hz, 1H),6.29 (s, 1H), 5.20 (q, J = 8.6 Hz, 4H), 3.60 (s, 3H). 4 Off-white118.1-119.3 ESIMS m/z 527 ¹H NMR (400 MHz, Solid ([M − H]⁺) Acetone-d₆)δ 11.84 (s, 1H), 7.41-7.28 (m, 1H), 6.66 (dd, J = 4.1, 0.9 Hz, 1H), 6.18(s, 1H), 5.54 (s, 2H), 5.02 (q, J = 8.6 Hz, 4H), 3.27 (s, 3H). 5Off-white 138.7-140.7 ESIMS m/z 555 ¹H NMR (400 MHz, Solid ([M − H]⁺)Acetone-d6) δ 12.00 (s, 1H), 7.32-7.24 (m, 1H), 6.69 (dd, J = 4.2, 0.9Hz, 1H), 6.23 (s, 1H), 6.16 (s, 2H), 5.02 (q, J = 8.6 Hz, 4H), 1.89 (s,3H). 6 Off-white 113.1-114.3 ESIMS m/z 513 ¹H NMR (400 MHz, Solid ([M +H]⁺) Acetone-d₆) δ 7.35- 7.24 (m, 1H), 6.73 (d, J = 4.2 Hz, 1H), 5.88(s, 1H), 4.76 (q, J = 8.7 Hz, 4H), 3.35 (s, 3H), 3.28 (s, 3H). 7Off-white 95.0-96.3 ESIMS m/z 512 ¹H NMR (400 MHz, Solid ([M—CH₂O]⁺)Acetone-d₆) δ 7.35- 7.24 (m, 1H), 6.73 (d, J = 4.2 Hz, 1H), 5.88 (s,1H), 4.76 (q, J = 8.7 Hz, 4H), 3.35 (s, 3H), 3.28 (s, 3H). 8 Off-white176.7-177.9 ESIMS m/z 512 ¹H NMR (400 MHz, Solid ([M—CH₂CO₂]⁺)Acetone-d₆) δ 7.32 (s, 1H), 6.76 (s, 1H), 6.00 (s, 1H), 5.83 (s, 2H),4.76 (d, J = 8.4 Hz, 4H), 3.30 (d, J = 3.1 Hz, 3H), 1.92 (s, 3H). 9Off-white 69.3-70.8 ESIMS m/z 512 ¹H NMR (400 MHz, Solid ([M—PhCHO]+)496 Acetone-d₆) δ 7.38- ([M—PhCH₂OCH₃]⁺) 7.01 (m, 6H), 6.75 (d, J = 4.1Hz, 1H), 5.96 (s, 1H), 5.46 (s, 2H), 4.79-4.57 (m, 6H), 3.34 (s, 3H). 10Pale IR (thin ESIMS m/z 649 ¹H NMR (400 MHz, Yellow film, cm⁻¹) ([M +H]⁺) Acetone-d₆) δ 7.29- Gum 1588, 7.08 (m, 6H), 6.82 1302 (d, J = 3.9Hz, 1H), 1265, 5.90 (s, 1H), 5.40 (s, 1150, 2H), 5.10 (s, 2H), 1066,4.79 (q, J = 8.7 Hz, 996, 4H), 4.69 (s, 2H), 958, 697 3.27 (s, 3H). 11Pale IR (thin ESIMS m/z 617 ¹H NMR (400 MHz, Yellow film, cm⁻¹)([M—PhCH₂O]⁺) Acetone-d₆) δ 7.29- Gum 1588, 7.05 (m, 11H), 6.87 1368 (d,J = 4.0 Hz, 1H), 1263 5.90 (s, 1H), 5.40 (s, 1150, 2H), 5.23 (s, 2H),1055, 4.75 (q, J = 8.7 Hz, 957, 4H), 4.69 (s, 2H), 738, 696 4.52 (s,2H). 12 Pale 180.9-182.6 ESIMS m/z 503 ¹H NMR (400 MHz, Yellow ([M +H]+) 501 Acetone-d₆) δ 10.97 Solid ([M − H]+) (s, 1H), 9.60 (s, 1H),7.26 (s, 1H), 6.63 (s, 1H), 5.10 (dd, J = 16.9, 8.4 Hz, 4H). 13 OffWhite 78.5-80.3 ESIMS m/z 517 ¹H NMR (400 MHz, Solid ([M + H]⁺) 515Acetone-d₆) δ 9.19 ([M − H]⁺) (bs, 1H), 17.34- 7.20 (m, 1H), 6.66 (d, J= 4.2 Hz, 1H), 4.92 (q, J = 8.6 Hz, 5H), 3.52 (s, 3H). 14 Off White132.8-135.5 ESIMS m/z 517 ¹H NMR (400 MHz, Solid ([M + H]⁺) 515Acetone-d₆) δ 11.81 ([M − H]⁺) (s, 1H), 7.44-7.39 (m, 1H), 6.78 (dd, J =4.1, 0.8 Hz, 1H), 5.29 (q, J = 8.5 Hz, 4H), 3.58 (s, 3H). 15 Off White124.6-126.3 ESIMS m/z 545 ¹H NMR (400 MHz, Solid ([M − H]⁺) Acetone-d₆)δ 11.38 (s, 1H), 7.42 (m, 1H), 6.81 (d, J = 4.1 Hz, 1H), 5.62 (s, 2H),5.25 (q, J = 8.5 Hz, 4H), 3.42 (s, 3H). 16 Off White 91.3-92.8 ESIMS m/z620 ¹H NMR (400 MHz, Solid ([M − H]⁺) Acetone-d₆) δ 11.21 (s, 1H),7.29-7.23 (m, 1H), 7.21-7.08 (m, 5H), 6.65 (dd, J = 4.1, 0.9 Hz, 1H),5.64 (s, 2H), 5.04 (q, J = 8.5 Hz, 4H), 4.59 (s, 2H). 17 Off White118.1-119.2 ESIMS m/z 531 ¹H NMR (400 MHz, Solid ([M + H]⁺) Acetone-d₆)δ 7.46 (s, 1H), 6.87 (s, 1H), 4.98 (q, J = 8.4 Hz, 4H), 3.52-3.43 (m,3H), 3.42-3.35 (m, 3H). 18 Off White 139.6-141.0 ESIMS m/z 530 ¹H NMR(400 MHz, Solid ([M—CH₂O]⁺) 514 Acetone-d₆) δ 7.47 ([M—CH₃OCH₃]⁺) (s,1H), 6.88 (s, 1H), 5.41 (s, 2H), 4.98 (q, J = 8.5 Hz, 4H), 3.49 (m, 6H).19 Off White 114.5-115.5 ESIMS m/z 530 ¹H NMR (400 MHz, Solid([M—CH₂CO₂]⁺) Acetone-d₆) δ 7.48 (s, 1H), 6.91 (s, 1H), 5.98-5.90 (m,2H), 5.12-4.85 (m, 4H), 3.57-3.36 (m, 3H), 2.18-1.98 (m, 4H). 20Off-White 237-241 ESIMS m/z 477 ¹H NMR (400 MHz, Solid ([M − H]⁺) (ClDMSO-d₆) δ 10.92 isomer), 523 (s, 1H), 10.49 (s, ([M − H]⁺) 1H), 6.55(s, 0.6H), (Br isomer) 6.53 (s, 0.4H), 6.30 (s, 1H), 5.15 (q, J = 8.9Hz, 6H), 2.67 (dd, J = 14.7, 7.3 Hz, 3H), 1.18 (t, J = 7.5 Hz, 4H). 21Off-White 81-83 ESIMS m/z 493 ¹H NMR (300 MHz, Solid ([M + H]⁺) DMSO-d₆)δ 10.09 (s, 1H), 6.63 (s, 1H), 6.25 (s, 1H), 5.03 (q, J = 9.0 Hz, 4H),3.39 (s, 3H), 2.69 (q, J = 7.5 Hz, 2H), 1.18 (t, J = 7.6 Hz, 3H). 22Off-White 224-228 ESIMS m/z 449 ¹H NMR (400 MHz, Solid ([M − H]⁺)DMSO-d₆) δ 11.05 (s, 1H), 10.57 (s, 1H), 6.93 (s, 1H), 6.51 (s, 1H),6.32 (s, 1H), 5.15 (d, J = 8.5 Hz, 4H). 23 Off-White 251-254 ESIMS m/z431 ¹H NMR (400 MHz, Solid ([M + H]⁺) DMSO-d₆) δ 10.91 (s, 1H), 10.39(s, 1H), 6.59-6.55 (m, 1H), 6.51 (d, J = 1.6 Hz, 1H), 6.30 (s, 1H), 5.14(q, J = 8.9 Hz, 4H), 2.14 (d, J = 0.8 Hz, 3H). 24 Off-White 269-271ESIMS m/z 440 ¹H NMR (300 MHz, Solid ([M − H]⁺) DMSO-d₆) δ 11.03 (bs,2H), 7.77 (d, J = 4.2 Hz, 1H), 6.75 (d, J = 4.2 Hz, 1H), 6.34 (s, 1H),5.15 (q, J = 8.9 Hz, 4H). 25 Off-White 231-234 ESIMS m/z 481 ¹H NMR (300MHz, Solid ([M + H]⁺) DMSO-d₆) δ 11.14 (s, 1H), 10.59 (s, 1H), 7.05 (s,1H), 6.36 (s, 1H), 5.10 (q, J = 8.9 Hz, 4H), 3.81 (s, 3H). 26 Off-White140-144 ESIMS m/z 539 ¹H NMR (300 MHz, Sod ([M − H]⁺) DMSO-d₆) δ 10.04(s, 1H), 7.76 (d, J = 8.6 Hz, 2H), 7.54- 7.39 (m, 3H), 7.23 (d, J = 1.7Hz, 1H), 6.25 (s, 1H), 5.03 (q, J = 9.0 Hz, 4H), 3.51 (s, 3H). 27Off-White 264-268 ESIMS m/z 440 ¹H NMR (400 MHz, Solid ([M − H]⁺)DMSO-d₆) δ 11.13 (s, 1H), 10.63 (s, 1H), 8.02 (d, J = 1.6 Hz, 1H), 6.99(d, J = 1.7 Hz, 1H), 6.34 (s, 1H), 5.16 (q, J = 8.9 Hz, 4H). 28 AshSolid 93-97 ESIMS m/z 465 ¹H NMR (400 MHz, ([M + H]⁺) DMSO-d₆) δ 9.42(s, 1H), 7.59 (d, J = 5.9 Hz, 1H), 7.05 (d, J = 5.9 Hz, 1H), 6.22 (s,1H), 5.02 (q, J = 9.0 Hz, 4H), 3.24 (s, 3H). 29 Off-White 115-118 ESIMSm/z 465 ¹H NMR (400 MHz, Solid ([M + H]⁺) (Cl DMSO-d₆) δ 10.16 isomer),510 (s, 1H), 7.16 (d, J = ([M + H]⁺) (Br 1.7 Hz, 0.2H), 7.05 isomer) (d,J = 1.7 Hz, 0.8H), 6.76 (d, J = 1.7 Hz, 0.2H), 6.74 (d, J = 1.7 Hz,0.8H), 6.27 (s, 1H), 5.03 (q, J = 9.0 Hz, 5H), 3.43 (s, 3H). 30 AshSolid 220 ESIMS m/z 575 ¹H NMR (400 MHz, (dec) ([M + H]⁺) DMSO-d₆) δ11.42 (s, 1H), 10.79 (s, 1H), 7.21 (s, 1H), 6.40 (s, 1H), 5.10 (q, J =8.8 Hz, 4H). 31 Pale ESIMS m/z 445 ¹H NMR (400 MHz, Yellow ([M + H]⁺)cdcl3) δ 7.33-7.12 Sticky (m, 2H), 6.91 (d, J = Solid 5.7 Hz, 1H), 5.94(s, 1H), 4.73 (q, J = 8.4 Hz, 4H), 3.30 (s, 3H), 2.17 (s, 3H). 32 AshSolid 240 ESIMS m/z 451 ¹H NMR (400 MHz, (dec) ([M + H]⁺) DMSO-d₆) δ11.16 (s, 1H), 10.69 (s, 1H), 7.18 (d, J = 5.8 Hz, 1H), 6.95 (d, J = 5.8Hz, 1H), 6.38 (s, 1H), 5.12 (q, J = 8.9 Hz, 4H). 33 Light- 253-257 ESIMSm/z 447 ¹H NMR (400 MHz, Green Solid ([M + H]⁺) DMSO-d₆) δ 10.81 (s,1H), 10.54 (s, 1H), 7.15-6.77 (m, 2H), 6.31 (s, 1H), 5.12 (q, J = 8.9Hz, 4H), 3.82 (s, 3H). 34 Off-White 136-139 ESIMS m/z 445 ¹H NMR (300MHz, Solid ([M + H]⁺) DMSO-d₆) δ 9.79 (s, 1H), 6.70 (s, 1H), 6.63 (d, J= 1.5 Hz, 1H), 6.22 (s, 1H), 5.02 (q, J = 9.0 Hz, 4H), 3.38 (s, 3H),2.17 (s, 3H). 35 Light- 107-110 ESIMS m/z 495 ¹H NMR (300 MHz, Yellow([M + H]⁺) DMSO-d₆) δ 9.53 (s, Solid 1H), 7.49 (s, 1H), 6.23 (s, 1H),5.03 (q, J = 9.0 Hz, 4H), 3.87 (d, J = 2.7 Hz, 3H), 3.24 (s, 3H). 36Brown 107-111 ESIMS m/z 461 ¹H NMR (300 MHz, Solid ([M + H]⁺) DMSO-d₆) δ8.78 (s, 1H), 7.40 (d, J = 6.1 Hz, 1H), 7.02 (d, J = 6.1 Hz, 1H), 6.19(s, 1H), 5.01 (q, J = 9.0 Hz, 4H), 3.83 (s, 3H), 3.15 (s, 3H). 37Off-White 249-253 ESIMS m/z 431 ¹H NMR (300 MHz, Solid ([M + H]⁺)DMSO-d₆) δ 10.68 (s, 1H), 10.36 (s, 1H), 6.97 (d, J = 5.5 Hz, 1H), 6.76(d, J = 5.5 Hz, 1H), 6.34 (s, 1H), 5.10 (q, J = 8.9 Hz, 4H), 2.17 (s,3H). 38 Light- 132-136 ESIMS m/z 454 ¹H NMR (400 MHz, Green Solid ([M −H]⁺) DMSO-d₆) δ 10.26 (s, 1H), 8.02 (d, J = 1.4 Hz, 1H), 7.08 (s, 1H),6.25 (s, 1H), 5.03 (q, J = 9.0 Hz, 4H), 3.46 (s, 3H). 39 Light 112-116ESIMS m/z 445 ¹H NMR (400 MHz, Brown ([M + H]⁺) DMSO-d₆) δ 9.62 (s,Solid 1H), 6.61 (s, 2H), 6.21 (s, 1H), 5.01 (q, J = 9.0 Hz, 4H), 3.34(s, 3H), 2.36 (s, 3H). 40 Off-White 269-272 ESIMS m/z 527 ¹H NMR (400MHz, Solid ([M + H]⁺) DMSO-d6) δ 11.13 (s, 1H), 10.52 (s, 1H), 7.64 (d,J = 8.5 Hz, 2H), 7.48 (d, J = 8.5 Hz, 2H), 7.39 (d, J = 1.5 Hz, 1H),7.07 (d, J = 1.5 Hz, 1H), 6.33 (s, 1H), 5.19 (q, J = 8.9 Hz, 4H). 41Off-White 247-250 ESIMS m/z 431 ¹H NMR (400 MHz, Solid ([M + H]⁺)DMSO-d₆) δ 10.84 (s, 1H), 10.37 (s, 1H), 6.55 (dd, J = 3.5, 1.0 Hz, 1H),6.46 (d, J = 3.6 Hz, 1H), 6.29 (s, 1H), 5.14 (q, J = 8.9 Hz, 4H), 2.35(s, 3H). 42 Off-White 237-240 ESIMS m/z 465 ¹H NMR (300 MHz, Solid ([M +H]⁺) DMSO-d₆) δ 10.85 (s, 1H), 10.42 (s, 1H), 7.08 (s, 1H), 6.36 (s,1H), 5.10 (q, J = 8.9 Hz, 4H), 2.13 (s, 3H). 43 Off-White 217-220 ESIMSm/z 449 ¹H NMR (400 MHz, Solid ([M − H]⁺) (Cl DMSO-d₆) δ 7.10 isomer),495 (d, J = 1.7 Hz, ([M − H]⁺) 0.2H), 6.99 (d, J = (Br isomer) 1.8 Hz,0.8H), 6.67- 6.64(m, 1H), 6.31 (s, 1H), 5.15 (q, J = 8.9 Hz, 4H). 44Off-White 210 ESIMS m/z 520 ¹H NMR (400 MHz, Solid (dec) ([M + H]⁺)DMSO-d₆) δ 11.46 (s, 1H), 10.86 (s, 1H), 6.41 (s, 1H), 5.12 (q, J = 8.8Hz, 4H). 45 Off-White 231-235 ESIMS m/z 495 ¹H NMR (400 MHz, Solid ([M +H]⁺) DMSO-d₆) δ 11.28 (s, 1H), 10.68 (s, 1H), 7.19 (d, J = 5.8 Hz, 1H),6.98 (d, J = 5.8 Hz, 1H), 6.39 (s, 1H), 5.11 (q, J = 8.8 Hz, 4H).

Example 9 Insecticidal Testing

Compounds 1-19 identified in Table 1 were tested against corn earworm(Helicoverpa zea) and beet armyworm (Spodoptera exigua), and Compounds20-45 were tested against beet armyworm (Spodoptera exigua) and cabbagelooper (Trichoplusia ni (Huebner)). Beet armyworm has few effectiveparasites, diseases, or predators to lower its population. Beet armyworminfests many weeds, trees, grasses, legumes, and field crops. In variousplaces, it is of economic concern upon asparagus, cotton, corn,soybeans, tobacco, alfalfa, sugar beets, peppers, tomatoes, potatoes,onions, peas, sunflowers, and citrus, among other plants. Corn earwormis known to attack corn and tomatoes, but it also attacks artichoke,asparagus, cabbage, cantaloupe, collards, cowpeas, cucumbers, eggplant,lettuce, lima beans, melon, okra, peas, peppers, potatoes, pumpkin, snapbeans, spinach, squash, sweet potatoes, and watermelon, among otherplants. Corn earworm is also known to be resistant to certaininsecticides. The cabbage looper is found throughout Canada, Mexico, andthe United States wherever crucifers are cultivated. Cabbage loopers areleaf feeders, and in the first three instars they confine their feedingto the lower leaf surface. The cabbage looper feeds on a wide variety ofcultivated plants and weeds. As the common name implies, it feedsreadily on crucifers, and has been reported damaging broccoli, cabbage,cauliflower, Chinese cabbage, collards, kale, mustard, radish, rutabaga,turnip, and watercress. Other vegetable crops injured include beet,cantaloupe, celery, cucumber, lima bean, lettuce, parsnip, pea, pepper,potato, snap bean, spinach, squash, sweet potato, tomato, andwatermelon. It is somewhat erratic in occurrence, typically veryabundant one year, and then scarce for two to three years. This islikely due to a nuclear polyhedrosis virus. The cabbage looper is highlydispersive, and adults have sometimes found at high altitudes and farfrom shore. Flight ranges of approximately 200 km have been estimated.Consequently, because of the above factors control of these pests isimportant. Furthermore, compounds that control these pests are useful incontrolling other pests.

The testing of Compounds 1-19 against corn earworm and beet armyworm wasconducted as follows. Bioassays were conducted using a 128 well diettray assay. To prepare test solutions, the test compound was formulatedat 2000 ppm solution as 4 mg/2 mL of 9 acetone:1 tap water. 50 μL of the2000 ppm (equivalent to 50 μg/cm² dose on diet surface area) testsolution was pipetted upon the surface of 1 mL of lepidopteran diet(Southland Multi-Species Lepidopteran Diet) contained in each of eightwells per insect species (one well=1 replication). A second-instar cornearworm and beet armyworm were placed upon the treated diet in each wellonce the solvent had air-dried. Trays containing the treated diet andlarvae were covered and then held in a growth chamber at 25° C., 50-55%RH, and 16 hr light:8 hr dark for 5 days. Observations were conducted 5days after treatment and infestation. The number of dead insects of 8per species per treatment was then determined using a dosing equivalentto 50 μg/cm² dose on diet surface area.

The testing of Compounds 20-45 against corn earworm and cabbage looperwas conducted as follows. Bioassays were conducted using a 128 well diettray assay. Test compounds were formulated at 2000 ppm solution as 4 mgof compound dissolved in 2 mL of 9 part acetone to 1 part tap water. 50μl of the 2000 ppm (equivalent to 50 μg/cm² dose on diet surface area)test solution was dispensed upon the surface of 1 mL of lepidopterandiet (Southland Multi-Species Lepidopteran Diet) contained in each ofeight wells per insect species (8 wells=1 replication). Acetone wasallowed to dry for 10-20 minutes in fume hood. A second-instar beatarmyworm and cabbage looper were placed upon the treated diet in eachwell once the solvent had dried. Trays containing the treated diet andlarvae were covered and then held in a growth chamber at 25° C., 50-55%RH, and 16 hour light:8 hour dark for 5 days. Observations wereconducted 5 days after treatment and infestation. The number of deadinsects of 8 per species per treatment was then determined.

For corn earworm, Compounds 1-2, 4-5, 7-10, 12-13 and 19 showed apercent control or mortality rate of between 80-100%. No activityagainst corn earworm was noticed in Compounds 3, 6, 11 and 14-18 in thepresent test. For beet armyworm, Compounds 2, 4-5, 7-10, 12-13, 15, 19,25-26, 32, 37, and 44 showed a percent control or mortality rate ofbetween 80-100%. Compounds 1, 28, and 45 showed some activity but it wasbelow the 80% threshold of the study. No activity was noticed againstbeet armyworm in Compounds 3, 6, 11, 14-16-18, 20-24, 27, 29-31, 33-36,and 38-43 in the present test. For cabbage looper, Compounds 25-26, 34,38-39, and 44 showed a percent control or mortality rate of between80-100%. Compounds 31 and 35-37 showed some activity but it was belowthe 80% threshold of the study. No activity was noticed in Compounds20-24, 27-30, 32-33, 40-43, and 45 in the present test.

The foregoing is illustrative of the present invention, and is not to beconstrued as limiting thereof. The invention is defined by the followingclaims, with equivalents of the claims to be included therein.

What is claimed is:
 1. A compound of formula (I):

wherein: R¹ is selected from the group consisting of hydrogen andhalogen; R² is selected from the group consisting of hydrogen,substituted or unsubstituted C₁-C₆ alkyl, substituted or unsubstitutedC₂-C₆ alkenyl, substituted or unsubstituted C₁-C₆ haloalkyl, substitutedor unsubstituted C₁-C₆ acyl, substituted or unsubstituted C₁-C₆carboalkoxy, carboxylic acid, substituted or unsubstituted C₂-C₆alkenyloxy, substituted or unsubstituted C₁-C₆ alkoxy, substituted orunsubstituted C₃-C₆ alkynyl, substituted or unsubstituted C₃-C₆alkynyloxy, substituted or unsubstituted C₃-C₁₀ aryl, substituted orunsubstituted C₁-C₁₀ aryloxy, substituted or unsubstituted C₃-C₁₀cycloalkenyl, substituted or unsubstituted C₃-C₁₀ cycloalkenyloxy,substituted or unsubstituted C₃-C₁₀ cycloalkyl, substituted orunsubstituted C₃-C₁₀ cycloalkoxy, halo, and substituted or unsubstitutedC₁-C₁₀ heterocyclyl; R³ is selected from the group consisting ofhydrogen, substituted or unsubstituted C₁-C₆ alkyl, substituted orunsubstituted C₂-C₆ alkenyl, substituted or unsubstituted C₁-C₆haloalkyl, substituted or unsubstituted C₃-C₆ acyl, substituted orunsubstituted C₁-C₆ carboalkoxy, carboxylic acid, substituted orunsubstituted C₂-C₆ alkenyloxy, substituted or unsubstituted C₁-C₆alkoxy, substituted or unsubstituted C₃-C₆ alkynyl, substituted orunsubstituted C₃-C₆ alkynyloxy, substituted or unsubstituted C₃-C₁₀aryl, substituted or unsubstituted C₃-C₁₀ aryloxy, substituted orunsubstituted C₃-C₁₀ cycloalkenyl, substituted or unsubstituted C₃-C₁₀cycloalkenyloxy, substituted or unsubstituted C₃-C₁₀ cycloalkyl,substituted or unsubstituted C₃-C₁₀ cycloalkoxy, halo, and substitutedor unsubstituted C₁-C₁₀ heterocyclyl; each of R⁴, R⁵, and R⁶ isindependently selected from the group consisting of hydrogen, halogen,substituted or unsubstituted C₁-C₆ alkyl, substituted or unsubstitutedC₂-C₆ alkenyl, substituted or unsubstituted C₁-C₆ haloalkyl, substitutedor unsubstituted C₁-C₆ acyl, substituted or unsubstituted C₁-C₆carboalkoxy, carboxylic acid, substituted or unsubstituted C₂-C₆alkenyloxy, substituted or unsubstituted C₁-C₆ alkoxy, substituted orunsubstituted C₃-C₆ alkynyl, substituted or unsubstituted C₃-C₆alkynyloxy, substituted or unsubstituted C₃-C₁₀ aryl, substituted orunsubstituted C₁-C₁₀ aryloxy, substituted or unsubstituted C₃-C₁₀cycloalkenyl, substituted or unsubstituted C₃-C₁₀ cycloalkenyloxy,substituted or unsubstituted C₃-C₁₀ cycloalkyl, substituted orunsubstituted C₃-C₁₀ cycloalkoxy, substituted or unsubstituted C₁-C₆nitriles, substituted or unsubstituted C₁-C₆ amides, substituted orunsubstituted C₁-C₆ amines, S (substituted or unsubstituted C₁-C₆alkyl), S(O)_(n) (substituted or unsubstituted C₁-C₆ alkyl) wherein n=0,1 or 2, and substituted or unsubstituted C₁-C₁₀ heterocyclyl; and eachR⁷ is independently selected from the group consisting of halogen,substituted or unsubstituted C₁-C₆ alkyl, substituted or unsubstitutedC₂-C₆ alkenyl, substituted or unsubstituted C₁-C₆ haloalkyl, substitutedor unsubstituted C₁-C₆ acyl, substituted or unsubstituted C₁-C₆carboalkoxy, carboxylic acid, substituted or unsubstituted substitutedor unsubstituted C₂-C₆ alkenyloxy, substituted or unsubstituted C₁-C₆alkoxy, substituted or unsubstituted C₃-C₆ alkynyl, substituted orunsubstituted C₃-C₆ alkynyloxy, substituted or unsubstituted C₃-C₁₀aryl, substituted or unsubstituted C₁-C₁₀ aryloxy, substituted orunsubstituted C₃-C₁₀ cycloalkenyl, substituted or unsubstituted C₃-C₁₀cycloalkenyloxy, substituted or unsubstituted C₃-C₁₀ cycloalkyl,substituted or unsubstituted C₃-C₁₀ cycloalkoxy, and substituted orunsubstituted C₁-C₁₀ heterocyclyl, wherein each substituted orunsubstituted substituent may be independently substituted with one ormore of the following substituents F, Cl, Br, I, CN, NO₂, C₁-C₆ alkyl,C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ alkoxy, C₁-C₆ haloalkyl, C₁-C₆haloalkoxy, C₁-C₆ haloalkylthio, S(═O)_(n1)C₁-C₆ alkyl (where n1=0-2),S(═O)_(n1)C₁-C₆ haloalkyl (where n1=0-2), OSO₂C₁-C₆ haloalkyl,C(═O)OC₁-C₆ alkyl, C(═O)C₁-C₆ alkyl, C(═O)C₁-C₆ haloalkyl, aryl, C₁-C₆hydroxyalkyl, CO₂R⁸, wherein R⁸ is a C₁-C₆ alkyl, and heterocyclyl.
 2. Acompound according to claim 1, wherein R⁷ represents halogen.
 3. Acompound according to claim 2, wherein R⁷ represents F.
 4. A compoundaccording to claim 1, wherein R⁵ represents substituted or unsubstitutedC₁-C₆ haloalkyl.
 5. A compound according to claim 4, wherein R⁵represents CF₃.
 6. A compound according to claim 1, wherein R²represents H, CH₂OCH₃, CH₂OC(═O)CH₃ or CH₂OCH₂R⁸, wherein R⁸ represents


7. A compound according to claim 6, wherein R³ represents H, methyl,CH₂OCH₃, or CH₂OCH₂R⁸, wherein R⁸ represents


8. A compound according to claim 1, wherein R⁵ represents CF₃, each ofR¹, R⁴, and R⁶ represents H, and R⁷ represents F.
 9. A compoundaccording to claim 8, wherein R³ represents H or methyl.
 10. Acomposition for controlling insects which comprises a compound accordingto claim 1 in combination with a phytologically-acceptable carrier. 11.A method of controlling insects which comprises applying to a locuswhere control is desired an insect-inactivating amount of a compoundaccording to claim
 1. 12. A composition which comprises a compoundaccording to claim 1 and at least one compound selected from the groupconsisting of fungicides, insecticides, nematocides, miticides,arthropodicides, and bactericides.
 13. A composition which comprises acompound according to claim 1 and one or more compounds selected from:(3-ethoxypropyl)mercury bromide, 1,2-dichloropropane,1,3-dichloropropene, 1-methylcyclopropene, 1-naphthol,2-(octylthio)ethanol, 2,3,5-tri-iodobenzoic acid, 2,3,6-TBA,2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA-potassium,2,3,6-TBA-sodium, 2,4,5-T, 2,4,5-T-2-butoxypropyl, 2,4,5-T-2-ethylhexyl,2,4,5-T-3-butoxypropyl, 2,4,5-TB, 2,4,5-T-butomethyl, 2,4,5-T-butotyl,2,4,5-T-butyl, 2,4,5-T-isobutyl, 2,4,5-T-isoctyl, 2,4,5-T-isopropyl,2,4,5-T-methyl, 2,4,5-T-pentyl, 2,4,5-T-sodium,2,4,5-T-triethylammonium, 2,4,5-T-trolamine, 2,4-D,2,4-D-2-butoxypropyl, 2,4-D-2-ethylhexyl, 2,4-D-3-butoxypropyl,2,4-D-ammonium, 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium,2,4-DB-isoctyl, 2,4-DB-potassium, 2,4-DB-sodium, 2,4-D-butotyl,2,4-D-butyl, 2,4-D-diethylammonium, 2,4-D-dimethylammonium,2,4-D-diolamine, 2,4-D-dodecylammonium, 2,4-DEB, 2,4-DEP, 2,4-D-ethyl,2,4-D-heptylammonium, 2,4-D-isobutyl, 2,4-D-isoctyl, 2,4-D-isopropyl,2,4-D-isopropylammonium, 2,4-D-lithium, 2,4-D-meptyl, 2,4-D-methyl,2,4-D-octyl, 2,4-D-pentyl, 2,4-D-potassium, 2,4-D-propyl, 2,4-D-sodium,2,4-D-tefuryl, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium,2,4-D-tris(2-hydroxypropyl)ammonium, 2,4-D-trolamine, 21P,2-methoxyethylmercury chloride, 2-phenylphenol, 3,4-DA, 3,4-DB, 3,4-DP,4-aminopyridine, 4-CPA, 4-CPA-potassium, 4-CPA-sodium, 4-CPB, 4-CPP,4-hydroxyphenethyl alcohol, 8-hydroxyquinoline sulfate,8-phenylmercurioxyquinoline, abamectin, abscisic acid, ACC, acephate,acequinocyl, acetamiprid, acethion, acetochlor, acetophos, acetoprole,acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-methyl,acifluorfen-sodium, aclonifen, acrep, acrinathrin, acrolein,acrylonitrile, acypetacs, acypetacs-copper, acypetacs-zinc, alachlor,alanycarb, albendazole, aldicarb, aldimorph, aldoxycarb, aldrin,allethrin, allicin, allidochlor, allosamidin, alloxydim,alloxydim-sodium, allyl alcohol, allyxycarb, alorac, alpha-cypermethrin,alpha-endosulfan, ametoctradin, ametridione, ametryn, amibuzin,amicarbazone, amicarthiazol, amidithion, amidoflumet, amidosulfuron,aminocarb, aminocyclopyrachlor, aminocyclopyrachlor-methyl,aminocyclopyrachlor-potassium, aminopyralid, aminopyralid-potassium,aminopyralid-tris(2-hydroxypropyl)ammonium, amiprofos-methyl,amiprophos, amisulbrom, amiton, amiton oxalate, amitraz, amitrole,ammonium sulfamate, ammonium α-naphthaleneacetate, amobam, ampropylfos,anabasine, ancymidol, anilazine, anilofos, anisuron, anthraquinone,antu, apholate, aramite, arsenous oxide, asomate, aspirin, asulam,asulam-potassium, asulam-sodium, athidathion, atraton, atrazine,aureofungin, aviglycine, aviglycine hydrochloride, azaconazole,azadirachtin, azafenidin, azamethiphos, azimsulfuron, azinphos-ethyl,azinphos-methyl, aziprotryne, azithiram, azobenzene, azocyclotin,azothoate, azoxystrobin, bachmedesh, barban, barium hexafluorosilicate,barium polysulfide, barthrin, BCPC, beflubutamid, benalaxyl,benalaxyl-M, benazolin, benazolin-dimethylammonium, benazolin-ethyl,benazolin-potassium, bencarbazone, benclothiaz, bendiocarb, benfluralin,benfuracarb, benfuresate, benodanil, benomyl, benoxacor, benoxafos,benquinox, bensulfuron, bensulfuron-methyl, bensulide, bensultap,bentaluron, bentazone, bentazone-sodium, benthiavalicarb,benthiavalicarb-isopropyl, benthiazole, bentranil, benzadox,benzadox-ammonium, benzalkonium chloride, benzamacril,benzamacril-isobutyl, benzamorf, benzfendizone, benzipram,benzobicyclon, benzofenap, benzofluor, benzohydroxamic acid,benzoximate, benzoylprop, benzoylprop-ethyl, benzthiazuron, benzylbenzoate, benzyladenine, berberine, berberine chloride, beta-cyfluthrin,beta-cypermethrin, bethoxazin, bicyclopyrone, bifenazate, bifenox,bifenthrin, bifujunzhi, bilanafos, bilanafos-sodium, binapacryl,bingqingxiao, bioallethrin, bioethanomethrin, biopermethrin,bioresmethrin, biphenyl, bisazir, bismerthiazol, bispyribac,bispyribac-sodium, bistrifluoron, bitertanol, bithionol, bixafen,blasticidin-S, borax, Bordeaux mixture, boric acid, boscalid,brassinolide, brassinolide-ethyl, brevicomin, brodifacoum,brofenvalerate, brofluthrinate, bromacil, bromacil-lithium,bromacil-sodium, bromadiolone, bromethalin, bromethrin, bromfenvinfos,bromoacetamide, bromobonil, bromobutide, bromocyclen, bromo-DDT,bromofenoxim, bromophos, bromophos-ethyl, bromopropylate, bromothalonil,bromoxynil, bromoxynil butyrate, bromoxynil heptanoate, bromoxyniloctanoate, bromoxynil-potassium, brompyrazon, bromuconazole, bronopol,bucarpolate, bufencarb, buminafos, bupirimate, buprofezin, Burgundymixture, busulfan, butacarb, butachlor, butafenacil, butamifos,butathiofos, butenachlor, butethrin, buthidazole, buthiobate, buthiuron,butocarboxim, butonate, butopyronoxyl, butoxycarboxim, butralin,butroxydim, buturon, butylamine, butylate, cacodylic acid, cadusafos,cafenstrole, calcium arsenate, calcium chlorate, calcium cyanamide,calcium polysulfide, calvinphos, cambendichlor, camphechlor, camphor,captafol, captan, carbamorph, carbanolate, carbaryl, carbasulam,carbendazim, carbendazim benzenesulfonate, carbendazim sulfite,carbetamide, carbofuran, carbon disulfide, carbon tetrachloride,carbophenothion, carbosulfan, carboxazole, carboxide, carboxin,carfentrazone, carfentrazone-ethyl, carpropamid, cartap, cartaphydrochloride, carvacrol, carvone, CDEA, cellocidin, CEPC, ceralure,Cheshunt mixture, chinomethionat, chitosan, chlobenthiazone,chlomethoxyfen, chloralose, chloramben, chloramben-ammonium,chloramben-diolamine, chloramben-methyl, chloramben-methylammonium,chloramben-sodium, chloramine phosphorus, chloramphenicol,chloraniformethan, chloranil, chloranocryl, chlorantraniliprole,chlorazifop, chlorazifop-propargyl, chlorazine, chlorbenside,chlorbenzuron, chlorbicyclen, chlorbromuron, chlorbufam, chlordane,chlordecone, chlordimeform, chlordimeform hydrochloride,chlorempenthrin, chlorethoxyfos, chloreturon, chlorfenac,chlorfenac-ammonium, chlorfenac-sodium, chlorfenapyr, chlorfenazole,chlorfenethol, chlorfenprop, chlorfenson, chlorfensulphide,chlorfenvinphos, chlorfluazuron, chlorflurazole, chlorfluren,chlorfluren-methyl, chlorflurenol, chlorflurenol-methyl, chloridazon,chlorimuron, chlorimuron-ethyl, chlormephos, chlormequat, chlormequatchloride, chlornidine, chlornitrofen, chlorobenzilate,chlorodinitronaphthalenes, chloroform, chloromebuform, chloromethiuron,chloroneb, chlorophacinone, chlorophacinone-sodium, chloropicrin,chloropon, chloropropylate, chlorothalonil, chlorotoluron, chloroxuron,chloroxynil, chlorphonium, chlorphonium chloride, chlorphoxim,chlorprazophos, chlorprocarb, chlorpropham, chlorpyrifos,chlorpyrifos-methyl, chlorquinox, chlorsulfuron, chlorthal,chlorthal-dimethyl, chlorthal-monomethyl, chlorthiamid, chlorthiophos,chlozolinate, choline chloride, chromafenozide, cinerin I, cinerin II,cinerins, cinidon-ethyl, cinmethylin, cinosulfuron, ciobutide,cisanilide, cismethrin, clethodim, climbazole, cliodinate, clodinafop,clodinafop-propargyl, cloethocarb, clofencet, clofencet-potassium,clofentezine, clofibric acid, clofop, clofop-isobutyl, clomazone,clomeprop, cloprop, cloproxydim, clopyralid, clopyralid-methyl,clopyralid-olamine, clopyralid-potassium,clopyralid-tris(2-hydroxypropyl)ammonium, cloquintocet,cloquintocet-mexyl, cloransulam, cloransulam-methyl, closantel,clothianidin, clotrimazole, cloxyfonac, cloxyfonac-sodium, CMA,codlelure, colophonate, copper acetate, copper acetoarsenite, copperarsenate, copper carbonate, basic, copper hydroxide, copper naphthenate,copper oleate, copper oxychloride, copper silicate, copper sulfate,copper zinc chromate, coumachlor, coumafuryl, coumaphos, coumatetralyl,coumithoate, coumoxystrobin, CPMC, CPMF, CPPC, credazine, cresol,crimidine, crotamiton, crotoxyphos, crufomate, cryolite, cue-lure,cufraneb, cumyluron, cuprobam, cuprous oxide, curcumenol, cyanamide,cyanatryn, cyanazine, cyanofenphos, cyanophos, cyanthoate,cyantraniliprole, cyazofamid, cybutryne, cyclafuramid, cyclanilide,cyclethrin, cycloate, cycloheximide, cycloprate, cycloprothrin,cyclosulfamuron, cycloxydim, cycluron, cyenopyrafen, cyflufenamid,cyflumetofen, cyfluthrin, cyhalofop, cyhalofop-butyl, cyhalothrin,cyhexatin, cymiazole, cymiazole hydrochloride, cymoxanil, cyometrinil,cypendazole, cypermethrin, cyperquat, cyperquat chloride, cyphenothrin,cyprazine, cyprazole, cyproconazole, cyprodinil, cyprofuram, cypromid,cyprosulfamide, cyromazine, cythioate, daimuron, dalapon,dalapon-calcium, dalapon-magnesium, dalapon-sodium, daminozide,dayoutong, dazomet, dazomet-sodium, DBCP, d-camphor, DCIP, DCPTA, DDT,debacarb, decafentin, decarbofuran, dehydroacetic acid, delachlor,deltamethrin, demephion, demephion-O, demephion-S, demeton,demeton-methyl, demeton-O, demeton-O-methyl, demeton-S,demeton-S-methyl, demeton-S-methylsulphon, desmedipham, desmetryn,d-fanshiluquebingjuzhi, diafenthiuron, dialifos, di-allate, diamidafos,diatomaceous earth, diazinon, dibutyl phthalate, dibutyl succinate,dicamba, dicamba-diglycolamine, dicamba-dimethylammonium,dicamba-diolamine, dicamba-isopropylammonium, dicamba-methyl,dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-trolamine,dicapthon, dichlobenil, dichlofenthion, dichlofluanid, dichlone,dichloralurea, dichlorbenzuron, dichlorflurenol, dichlorflurenol-methyl,dichlormate, dichlormid, dichlorophen, dichlorprop,dichlorprop-2-ethylhexyl, dichlorprop-butotyl,dichlorprop-dimethylammonium, dichlorprop-ethylammonium,dichlorprop-isoctyl, dichlorprop-methyl, dichlorprop-P,dichlorprop-P-2-ethylhexyl, dichlorprop-P-dimethylammonium,dichlorprop-potassium, dichlorprop-sodium, dichlorvos, dichlozoline,diclobutrazol, diclocymet, diclofop, diclofop-methyl, diclomezine,diclomezine-sodium, dicloran, diclosulam, dicofol, dicoumarol, dicresyl,dicrotophos, dicyclanil, dicyclonon, dieldrin, dienochlor, diethamquat,diethamquat dichloride, diethatyl, diethatyl-ethyl, diethofencarb,dietholate, diethyl pyrocarbonate, diethyltoluamide, difenacoum,difenoconazole, difenopenten, difenopenten-ethyl, difenoxuron,difenzoquat, difenzoquat metilsulfate, difethialone, diflovidazin,diflubenzuron, diflufenican, diflufenzopyr, diflufenzopyr-sodium,diflumetorim, dikegulac, dikegulac-sodium, dilor, dimatif, dimefluthrin,dimefox, dimefuron, dimepiperate, dimetachlone, dimetan, dimethacarb,dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin,dimethirimol, dimethoate, dimethomorph, dimethrin, dimethyl carbate,dimethyl phthalate, dimethylvinphos, dimetilan, dimexano, dimidazon,dimoxystrobin, dinex, dinex-diclexine, dingjunezuo, diniconazole,diniconazole-M, dinitramine, dinobuton, dinocap, dinocap-4, dinocap-6,dinocton, dinofenate, dinopenton, dinoprop, dinosam, dinoseb, dinosebacetate, dinoseb-ammonium, dinoseb-diolamine, dinoseb-sodium,dinoseb-trolamine, dinosulfon, dinotefuran, dinoterb, dinoterb acetate,dinoterbon, diofenolan, dioxabenzofos, dioxacarb, dioxathion,diphacinone, diphacinone-sodium, diphenamid, diphenyl sulfone,diphenylamine, dipropalin, dipropetryn, dipyrithione, diquat, diquatdibromide, disparlure, disul, disulfuram, disulfoton, disul-sodium,ditalimfos, dithianon, dithicrofos, dithioether, dithiopyr, diuron,d-limonene, DMPA, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium,dodemorph, dodemorph acetate, dodemorph benzoate, dodicin, dodicinhydrochloride, dodicin-sodium, dodine, dofenapyn, dominicalure,doramectin, drazoxolon, DSMA, dufulin, EBEP, EBP, ecdysterone,edifenphos, eglinazine, eglinazine-ethyl, emamectin, emamectin benzoate,EMPC, empenthrin, endosulfan, endothal, endothal-diammonium,endothal-dipotassium, endothal-disodium, endothion, endrin,enestroburin, EPN, epocholeone, epofenonane, epoxiconazole,eprinomectin, epronaz, EPTC, erbon, ergocalciferol, erlujixiancaoan,esdepallethrine, esfenvalerate, esprocarb, etacelasil, etaconazole,etaphos, etem, ethaboxam, ethachlor, ethalfluralin, ethametsulfuron,ethametsulfuron-methyl, ethaprochlor, ethephon, ethidimuron,ethiofencarb, ethiolate, ethion, ethiozin, ethiprole, ethirimol,ethoate-methyl, ethofumesate, ethohexadiol, ethoprophos, ethoxyfen,ethoxyfen-ethyl, ethoxyquin, ethoxysulfuron, ethychlozate, ethylformate, ethyl α-naphthaleneacetate, ethyl-DDD, ethylene, ethylenedibromide, ethylene dichloride, ethylene oxide, ethylicin, ethylmercury2,3-dihydroxypropyl mercaptide, ethylmercury acetate, ethylmercurybromide, ethylmercury chloride, ethylmercury phosphate, etinofen,etnipromid, etobenzanid, etofenprox, etoxazole, etridiazole, etrimfos,eugenol, EXD, famoxadone, famphur, fenamidone, fenaminosulf, fenamiphos,fenapanil, fenarimol, fenasulam, fenazaflor, fenazaquin, fenbuconazole,fenbutatin oxide, fenchlorazole, fenchlorazole-ethyl, fenchlorphos,fenclorim, fenethacarb, fenfluthrin, fenfuram, fenhexamid, fenitropan,fenitrothion, fenjuntong, fenobucarb, fenoprop, fenoprop-3-butoxypropyl,fenoprop-butomethyl, fenoprop-butotyl, fenoprop-butyl, fenoprop-isoctyl,fenoprop-methyl, fenoprop-potassium, fenothiocarb, fenoxacrim,fenoxanil, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P,fenoxaprop-P-ethyl, fenoxasulfone, fenoxycarb, fenpiclonil,fenpirithrin, fenpropathrin, fenpropidin, fenpropimorph, fenpyrazamine,fenpyroximate, fenridazon, fenridazon-potassium, fenridazon-propyl,fenson, fensulfothion, fenteracol, fenthiaprop, fenthiaprop-ethyl,fenthion, fenthion-ethyl, fentin, fentin acetate, fentin chloride,fentin hydroxide, fentrazamide, fentrifanil, fenuron, fenuron TCA,fenvalerate, ferbam, ferimzone, ferrous sulfate, fipronil, flamprop,flamprop-isopropyl, flamprop-M, flamprop-methyl, flamprop-M-isopropyl,flamprop-M-methyl, flazasulfuron, flocoumafen, flometoquin, flonicamid,florasulam, fluacrypyrim, fluazifop, fluazifop-butyl, fluazifop-methyl,fluazifop-P, fluazifop-P-butyl, fluazinam, fluazolate, fluazuron,flubendiamide, flubenzimine, flucarbazone, flucarbazone-sodium,flucetosulfuron, fluchloralin, flucofuron, flucycloxuron, flucythrinate,fludioxonil, fluenetil, fluensulfone, flufenacet, flufenerim,flufenican, flufenoxuron, flufenprox, flufenpyr, flufenpyr-ethyl,flufiprole, flumethrin, flumetover, flumetralin, flumetsulam, flumezin,flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, flumorph,fluometuron, fluopicolide, fluopyram, fluorbenside, fluoridamid,fluoroacetamide, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl,fluoroimide, fluoromidine, fluoronitrofen, fluothiuron, fluotrimazole,fluoxastrobin, flupoxam, flupropacil, flupropadine, flupropanate,flupropanate-sodium, flupyradifurone, flupyrsulfuron,flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, fluquinconazole,flurazole, flurenol, flurenol-butyl, flurenol-methyl, fluridone,fluorochloridone, fluoroxypyr, fluoroxypyr-butomethyl,fluoroxypyr-meptyl, flurprimidol, flursulamid, flurtamone, flusilazole,flusulfamide, fluthiacet, fluthiacet-methyl, flutianil, flutolanil,flutriafol, fluvalinate, fluxapyroxad, fluxofenim, folpet, fomesafen,fomesafen-sodium, fonofos, foramsulfuron, forchlorfenuron, formaldehyde,formetanate, formetanate hydrochloride, formothion, formparanate,formparanate hydrochloride, fosamine, fosamine-ammonium, fosetyl,fosetyl-aluminum, fosmethilan, fospirate, fosthiazate, fosthietan,frontalin, fuberidazole, fucaojing, fucaomi, funaihecaoling,fuphenthiourea, furalane, furalaxyl, furamethrin, furametpyr,furathiocarb, furcarbanil, furconazole, furconazole-cis, furethrin,furfural, furilazole, furmecyclox, furophanate, furyloxyfen,gamma-cyhalothrin, gamma-HCH, genit, gibberellic acid, gibberellins,gliftor, glufosinate, glufosinate-ammonium, glufosinate-P,glufosinate-P-ammonium, glufosinate-P-sodium, glyodin, glyoxime,glyphosate, glyphosate-diammonium, glyphosate-dimethylammonium,glyphosate-isopropylammonium, glyphosate-monoammonium,glyphosate-potassium, glyphosate-sesquisodium, glyphosate-trimesium,glyphosine, gossyplure, grandlure, griseofulvin, guazatine, guazatineacetates, halacrinate, halfenprox, halofenozide, halosafen,halosulfuron, halosulfuron-methyl, haloxydine, haloxyfop,haloxyfop-etotyl, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-etotyl,haloxyfop-P-methyl, haloxyfop-sodium, HCH, hemel, hempa, HEOD,heptachlor, heptenophos, heptopargil, heterophos, hexachloroacetone,hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole,hexaflumuron, hexaflurate, hexylure, hexamide, hexazinone, hexylthiofos,hexythiazox, HHDN, holosulf, huancaiwo, huangcaoling, huanjunzuo,hydramethylnon, hydrargaphen, hydrated lime, hydrogen cyanide,hydroprene, hymexazol, hyquincarb, IAA, IBA, icaridin, imazalil,imazalil nitrate, imazalil sulfate, imazamethabenz,imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic,imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin,imazaquin-ammonium, imazaquin-methyl, imazaquin-sodium, imazethapyr,imazethapyr-ammonium, imazosulfuron, imibenconazole, imicyafos,imidacloprid, imidaclothiz, iminoctadine, iminoctadine triacetate,iminoctadine trialbesilate, imiprothrin, inabenfide, indanofan,indaziflam, indoxacarb, inezin, iodobonil, iodocarb, iodomethane,iodosulfuron, iodosulfuron-methyl, iodosulfuron-methyl-sodium,iofensulfuron, iofensulfuron-sodium, ioxynil, ioxynil octanoate,ioxynil-lithium, ioxynil-sodium, ipazine, ipconazole, ipfencarbazone,iprobenfos, iprodione, iprovalicarb, iprymidam, ipsdienol, ipsenol,IPSP, isamidofos, isazofos, isobenzan, isocarbamid, isocarbophos,isocil, isodrin, isofenphos, isofenphos-methyl, isolan, isomethiozin,isonoruron, isopolinate, isoprocarb, isopropalin, isoprothiolane,isoproturon, isopyrazam, isopyrimol, isothioate, isotianil, isouron,isovaledione, isoxaben, isoxachlortole, isoxadifen, isoxadifen-ethyl,isoxaflutole, isoxapyrifop, isoxathion, ivermectin, izopamfos,japonilure, japothrins, jasmolin I, jasmolin II, jasmonic acid,jiahuangchongzong, jiajizengxiaolin, jiaxiangjunzhi, jiecaowan,jiecaoxi, jodfenphos, juvenile hormone I, juvenile hormone II, juvenilehormone III, kadethrin, karbutilate, karetazan, karetazan-potassium,kasugamycin, kasugamycin hydrochloride, kejunlin, kelevan, ketospiradox,ketospiradox-potassium, kinetin, kinoprene, kresoxim-methyl, kuicaoxi,lactofen, lambda-cyhalothrin, latilure, lead arsenate, lenacil,lepimectin, leptophos, lindane, lineatin, linuron, lirimfos, litlure,looplure, lufenuron, lvdingjunzhi, lvxiancaolin, lythidathion, MAA,malathion, maleic hydrazide, malonoben, maltodextrin, MAMA, mancopper,mancozeb, mandipropamid, maneb, matrine, mazidox, MCPA,MCPA-2-ethylhexyl, MCPA-butotyl, MCPA-butyl, MCPA-dimethylammonium,MCPA-diolamine, MCPA-ethyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl,MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium, MCPA-thioethyl,MCPA-trolamine, MCPB, MCPB-ethyl, MCPB-methyl, MCPB-sodium, mebenil,mecarbam, mecarbinzid, mecarphon, mecoprop, mecoprop-2-ethylhexyl,mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl,mecoprop-isoctyl, mecoprop-methyl, mecoprop-P, mecoprop-P-2-ethylhexyl,mecoprop-P-dimethylammonium, mecoprop-P-isobutyl, mecoprop-potassium,mecoprop-P-potassium, mecoprop-sodium, mecoprop-trolamine, medimeform,medinoterb, medinoterb acetate, medlure, mefenacet, mefenpyr,mefenpyr-diethyl, mefluidide, mefluidide-diolamine,mefluidide-potassium, megatomoic acid, menazon, mepanipyrim,meperfluthrin, mephenate, mephosfolan, mepiquat, mepiquat chloride,mepiquat pentaborate, mepronil, meptyldinocap, mercuric chloride,mercuric oxide, mercurous chloride, merphos, mesoprazine, mesosulfuron,mesosulfuron-methyl, mesotrione, mesulfen, mesulfenfos, metaflumizone,metalaxyl, metalaxyl-M, metaldehyde, metam, metam-ammonium, metamifop,metamitron, metam-potassium, metam-sodium, metazachlor, metazosulfuron,metazoxolon, metconazole, metepa, metflurazon, methabenzthiazuron,methacrifos, methalpropalin, methamidophos, methasulfocarb, methazole,methfuroxam, methidathion, methiobencarb, methiocarb,methiopyrisulfuron, methiotepa, methiozolin, methiuron, methocrotophos,methometon, methomyl, methoprene, methoprotryne, methoquin-butyl,methothrin, methoxychlor, methoxyfenozide, methoxyphenone, methylapholate, methyl bromide, methyl eugenol, methyl iodide, methylisothiocyanate, methylacetophos, methylchloroform, methyldymron,methylene chloride, methylmercury benzoate, methylmercury dicyandiamide,methylmercury pentachlorophenoxide, methylneodecanamide, metiram,metobenzuron, metobromuron, metofluthrin, metolachlor, metolcarb,metominostrobin, metosulam, metoxadiazone, metoxuron, metrafenone,metribuzin, metsulfovax, metsulfuron, metsulfuron-methyl, mevinphos,mexacarbate, mieshuan, milbemectin, milbemycin oxime, milneb, mipafox,mirex, MNAF, moguchun, molinate, molosultap, monalide, monisouron,monochloroacetic acid, monocrotophos, monolinuron, monosulfuron,monosulfuron-ester, monuron, monuron TCA, morfamquat, morfamquatdichloride, moroxydine, moroxydine hydrochloride, morphothion, morzid,moxidectin, MSMA, muscalure, myclobutanil, myclozolin,N-(ethylmercury)-p-toluenesulphonanilide, nabam, naftalofos, naled,naphthalene, naphthaleneacetamide, naphthalic anhydride, naphthoxyaceticacids, naproanilide, napropamide, naptalam, naptalam-sodium, natamycin,neburon, niclosamide, niclosamide-olamine, nicosulfuron, nicotine,nifluridide, nipyraclofen, nitenpyram, nithiazine, nitralin, nitrapyrin,nitrilacarb, nitrofen, nitrofluorfen, nitrostyrene, nitrothal-isopropyl,norbormide, norflurazon, nornicotine, noruron, novaluron, noviflumuron,nuarimol, OCH, octachlorodipropyl ether, octhilinone, ofurace,omethoate, orbencarb, orfralure, ortho-dichlorobenzene, orthosulfamuron,oryctalure, orysastrobin, oryzalin, osthol, ostramone, oxabetrinil,oxadiargyl, oxadiazon, oxadixyl, oxamate, oxamyl, oxapyrazon,oxapyrazon-dimolamine, oxapyrazon-sodium, oxasulfuron, oxaziclomefone,oxine-copper, oxolinic acid, oxpoconazole, oxpoconazole fumarate,oxycarboxin, oxydemeton-methyl, oxydeprofos, oxydisulfoton, oxyfluorfen,oxymatrine, oxytetracycline, oxytetracycline hydrochloride,paclobutrazol, paichongding, para-dichlorobenzene, parafluoron,paraquat, paraquat dichloride, paraquat dimetilsulfate, parathion,parathion-methyl, parinol, pebulate, pefurazoate, pelargonic acid,penconazole, pencycuron, pendimethalin, penflufen, penfluoron,penoxsulam, pentachlorophenol, pentanochlor, penthiopyrad, pentmethrin,pentoxazone, perfluidone, permethrin, pethoxamid, phenamacril, phenazineoxide, phenisopham, phenkapton, phenmedipham, phenmedipham-ethyl,phenobenzuron, phenothrin, phenproxide, phenthoate, phenylmercuriurea,phenylmercury acetate, phenylmercury chloride, phenylmercury derivativeof pyrocatechol, phenylmercury nitrate, phenylmercury salicylate,phorate, phosacetim, phosalone, phosdiphen, phosfolan, phosfolan-methyl,phosglycin, phosmet, phosnichlor, phosphamidon, phosphine, phosphocarb,phosphorus, phostin, phoxim, phoxim-methyl, phthalide, picloram,picloram-2-ethylhexyl, picloram-isoctyl, picloram-methyl,picloram-olamine, picloram-potassium, picloram-triethylammonium,picloram-tris(2-hydroxypropyl)ammonium, picolinafen, picoxystrobin,pindone, pindone-sodium, pinoxaden, piperalin, piperonyl butoxide,piperonyl cyclonene, piperophos, piproctanyl, piproctanyl bromide,piprotal, pirimetaphos, pirimicarb, pirimioxyphos, pirimiphos-ethyl,pirimiphos-methyl, plifenate, polycarbamate, polyoxins, polyoxorim,polyoxorim-zinc, polythialan, potassium arsenite, potassium azide,potassium cyanate, potassium gibberellate, potassium naphthenate,potassium polysulfide, potassium thiocyanate, potassiumα-naphthaleneacetate, pp′-DDT, prallethrin, precocene I, precocene II,precocene III, pretilachlor, primidophos, primisulfuron,primisulfuron-methyl, probenazole, prochloraz, prochloraz-manganese,proclonol, procyazine, procymidone, prodiamine, profenofos, profluazol,profluralin, profluthrin, profoxydim, proglinazine, proglinazine-ethyl,prohexadione, prohexadione-calcium, prohydrojasmon, promacyl, promecarb,prometon, prometryn, promurit, propachlor, propamidine, propamidinedihydrochloride, propamocarb, propamocarb hydrochloride, propanil,propaphos, propaquizafop, propargite, proparthrin, propazine,propetamphos, propham, propiconazole, propineb, propisochlor, propoxur,propoxycarbazone, propoxycarbazone-sodium, propyl isome,propyrisulfuron, propyzamide, proquinazid, prosuler, prosulfalin,prosulfocarb, prosulfuron, prothidathion, prothiocarb, prothiocarbhydrochloride, prothioconazole, prothiofos, prothoate, protrifenbute,proxan, proxan-sodium, prynachlor, pydanon, pymetrozine, pyracarbolid,pyraclofos, pyraclonil, pyraclostrobin, pyraflufen, pyraflufen-ethyl,pyrafluprole, pyramat, pyrametostrobin, pyraoxystrobin, pyrasulfotole,pyrazolynate, pyrazophos, pyrazosulfuron, pyrazosulfuron-ethyl,pyrazothion, pyrazoxyfen, pyresmethrin, pyrethrin I, pyrethrin II,pyrethrins, pyribambenz-isopropyl, pyribambenz-propyl, pyribencarb,pyribenzoxim, pyributicarb, pyriclor, pyridaben, pyridafol, pyridalyl,pyridaphenthion, pyridate, pyridinitril, pyrifenox, pyrifluquinazon,pyriftalid, pyrimethanil, pyrimidifen, pyriminobac, pyriminobac-methyl,pyrimisulfan, pyrimitate, pyrinuron, pyriofenone, pyriprole,pyripropanol, pyriproxyfen, pyrithiobac, pyrithiobac-sodium, pyrolan,pyroquilon, pyroxasulfone, pyroxsulam, pyroxychlor, pyroxyfur, quassia,quinacetol, quinacetol sulfate, quinalphos, quinalphos-methyl,quinazamid, quinclorac, quinconazole, quinmerac, quinoclamine,quinonamid, quinothion, quinoxyfen, quintiofos, quintozene, quizalofop,quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl,quizalofop-P-tefuryl, quwenzhi, quyingding, rabenzazole, rafoxanide,rebemide, resmethrin, rhodethanil, rhodojaponin-III, ribavirin,rimsulfuron, rotenone, ryania, saflufenacil, saijunmao, saisentong,salicylanilide, sanguinarine, santonin, schradan, scilliroside,sebuthylazine, secbumeton, sedaxane, selamectin, semiamitraz,semiamitraz chloride, sesamex, sesamolin, sethoxydim, shuangjiaancaolin,siduron, siglure, silafluofen, silatrane, silica gel, silthiofam,simazine, simeconazole, simeton, simetryn, sintofen, SMA, S-metolachlor,sodium arsenite, sodium azide, sodium chlorate, sodium fluoride, sodiumfluoroacetate, sodium hexafluorosilicate, sodium naphthenate, sodiumorthophenylphenoxide, sodium pentachlorophenoxide, sodium polysulfide,sodium thiocyanate, sodium α-naphthaleneacetate, sophamide, spinetoram,spinosad, spirodiclofen, spiromesifen, spirotetramat, spiroxamine,streptomycin, streptomycin sesquisulfate, strychnine, sulcatol,sulcofuron, sulcofuron-sodium, sulcotrione, sulfallate, sulfentrazone,sulfuram, sulfluramid, sulfometuron, sulfometuron-methyl, sulfosulfuron,sulfotep, sulfoxaflor, sulfoxide, sulfoxime, sulfur, sulfuric acid,sulfuryl fluoride, sulglycapin, sulprofos, sultropen, swep,tau-fluvalinate, tavron, tazimcarb, TCA, TCA-ammonium, TCA-calcium,TCA-ethadyl, TCA-magnesium, TCA-sodium, TDE, tebuconazole, tebufenozide,tebufenpyrad, tebufloquin, tebupirimfos, tebutam, tebuthiuron,tecloftalam, tecnazene, tecoram, teflubenzuron, tefluthrin,tefuryltrione, tembotrione, temephos, tepa, TEPP, tepraloxydim,terallethrin, terbacil, terbucarb, terbuchlor, terbufos, terbumeton,terbuthylazine, terbutryn, tetcyclacis, tetrachloroethane,tetrachlorvinphos, tetraconazole, tetradifon, tetrafluoron,tetramethrin, tetramethylfluthrin, tetramine, tetranactin, tetrasul,thallium sulfate, thenylchlor, theta-cypermethrin, thiabendazole,thiacloprid, thiadifluor, thiamethoxam, thiapronil, thiazafluoron,thiazopyr, thicrofos, thicyofen, thidiazimin, thidiazuron,thiencarbazone, thiencarbazone-methyl, thifensulfuron,thifensulfuron-methyl, thifluzamide, thiobencarb, thiocarboxime,thiochlorfenphim, thiocyclam, thiocyclam hydrochloride, thiocyclamoxalate, thiodiazole-copper, thiodicarb, thiofanox, thiofluoximate,thiohempa, thiomersal, thiometon, thionazin, thiophanate,thiophanate-methyl, thioquinox, thiosemicarbazide, thiosultap,thiosultap-diammonium, thiosultap-disodium, thiosultap-monosodium,thiotepa, thiram, thuringiensin, tiadinil, tiaojiean, tiocarbazil,tioclorim, tioxymid, tirpate, tolclofos-methyl, tolfenpyrad,tolylfluanid, tolylmercury acetate, topramezone, tralkoxydim,tralocythrin, tralomethrin, tralopyril, transfluthrin, transpermethrin,tretamine, triacontanol, triadimefon, triadimenol, triafamone,tri-allate, triamiphos, triapenthenol, triarathene, triarimol,triasulfuron, triazamate, triazbutil, triaziflam, triazophos,triazoxide, tribenuron, tribenuron-methyl, tribufos, tributyltin oxide,tricamba, trichlamide, trichlorfon, trichlormetaphos-3, trichloronat,triclopyr, triclopyr-butotyl, triclopyr-ethyl,triclopyr-triethylammonium, tricyclazole, tridemorph, tridiphane,trietazine, trifenmorph, trifenofos, trifloxystrobin, trifloxysulfuron,trifloxysulfuron-sodium, triflumizole, triflumuron, trifluralin,triflusulfuron, triflusulfuron-methyl, trifop, trifop-methyl,trifopsime, triforine, trihydroxytriazine, trimedlure, trimethacarb,trimeturon, trinexapac, trinexapac-ethyl, triprene, tripropindan,triptolide, tritac, triticonazole, tritosulfuron, trunc-call,uniconazole, uniconazole-P, urbacide, uredepa, valerate, validamycin,valifenalate, valone, vamidothion, vangard, vaniliprole, vernolate,vinclozolin, warfarin, warfarin-potassium, warfarin-sodium,xiaochongliulin, xinjunan, xiwojunan, XMC, xylachlor, xylenols,xylylcarb, yishijing, zarilamid, zeatin, zengxiaoan, zeta-cypermethrin,zinc naphthenate, zinc phosphide, zinc thiazole, zineb, ziram,zolaprofos, zoxamide, zuomihuanglong, α-chlorohydrin, α-ecdysone,α-multistriatin, and α-naphthaleneacetic acid.